Isothiazoline compounds for combating invertebrate pests

ABSTRACT

The present invention relates to isothiazoline compounds of formula I 
     
       
         
         
             
             
         
       
         
         wherein the variables are as defined in the claims or the description, 
         which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes, and to a method for producing them. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

This application is a National Stage application of InternationalApplication No. PCT/EP2012/076539, filed Dec. 21, 2012, which claims thebenefit of U.S. Provisional Application No. 61/579,676, filed Dec. 23,2011, the entire contents of which are hereby incorporated herein byreference.

The present invention relates to isothiazoline compounds which areuseful for combating or controlling invertebrate pests, in particulararthropod pests and nematodes, and to a method for producing them. Theinvention also relates to a method for controlling invertebrate pests byusing these compounds and to plant propagation material and to anagricultural and a veterinary composition comprising said compounds.

Invertebrate pests and in particular arthropods and nematodes destroygrowing and harvested crops and attack wooden dwelling and commercialstructures, causing large economic loss to the food supply and toproperty. While a large number of pesticidal agents are known, due tothe ability of target pests to develop resistance to said agents, thereis an ongoing need for new agents for combating invertebrate pests, inparticular insects, arachnids and nematodes.

Related insecticidal aryl azoline compounds are described in WO2011/092287, WO 2011/073444, WO 2010/090344, WO 2009/112275 and WO97/23212. However, these documents do not describe compounds having thecharacteristic substituents and substituents' arrangement as claimed inthe present invention.

It is an object of the present invention to provide compounds that havea good pesticidal activity, in particular insecticidal activity, andshow a broad activity spectrum against a large number of differentinvertebrate pests, especially against difficult to control arthropodpests and/or nematodes.

The object of the present invention was moreover to provide compoundswhich are less persistent, bioaccumulative and/or toxic than thecompounds of the prior art. Especially isoxazoline insecticides show ahigh persistency in the soil and thus accumulate there.

It has been found that these objectives can be achieved by isothiazolinecompounds of the formula I below, by their steroisomers and by theirsalts, in particular their agriculturally or veterinarily acceptablesalts.

Therefore, in a first aspect, the invention relates to isothiazolinecompounds of formula I

wherein

-   A is a group A¹, A², A³ or A⁴;    -   wherein    -   A¹ is selected from the group consisting of —C(═NR⁶)R⁸,        —S(O)_(n)R⁹ and —N(R⁵)R⁶;    -   A² is a group of following formula:

-   -   -   wherein        -   # denotes the bond to the aromatic ring of formula (I);        -   W is selected from O and S;        -   Y is selected from hydrogen, —N(R⁵)R⁶ and —OR⁹;

    -   A³ is a group of following formula:

-   -   -   wherein        -   # denotes the bond to the aromatic ring of formula (I);

    -   A⁴ is a 3-, 4-, 5-, 6- or 7-membered saturated, partially        unsaturated or maximally unsaturated heteromonocyclic ring        containing 1, 2, 3 or 4 heteroatoms or heteroatom groups        selected from N, O, S, NO, SO and SO₂, as ring members, or is a        8-, 9- or 10-membered saturated, partially unsaturated or        maximally unsaturated heterobicyclic ring containing 1, 2, 3 or        4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO        and SO₂, as ring members, where the heteromonocyclic or        heterobicyclic ring is optionally substituted with one or more,        preferably 1, 2 or 3, in particular 1, substituents R¹¹;

-   B¹, B² and B³ are each independently selected from the group    consisting of N and CR², with the proviso that at most two of B¹, B²    and B³ are N;

-   G¹, G², G³ and G⁴ are each independently selected from the group    consisting of N and CR⁴, with the proviso that at most two of G¹,    G², G³ and G⁴ are N;

-   R¹ is selected from the group consisting of C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₁-C₄-haloalkoxy-C₁-C₄-alkyl-, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,    C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl,    C₃-C₆-halocycloalkyl and —C(═O)OR¹⁵;

-   each R² is independently selected from the group consisting of    hydrogen, halogen, cyano, azido, nitro, —SCN, —SF₅, C₁-C₆-alkyl,    C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the four    last mentioned aliphatic and cycloaliphatic radicals may be    partially or fully halogenated and/or may be substituted by one or    more, preferably 1, 2 or 3, in particular 1, radicals R⁸,    -   —Si(R¹²)₃, —OR⁹, —S(O)_(n)R⁹, —NR^(10a)R^(10b),    -   phenyl which may be substituted by 1, 2, 3, 4 or 5, preferably        1, 2 or 3, in particular 1, radicals R¹¹, and a 3-, 4-, 5-, 6-        7-, 8-, 9- or 10-membered saturated, partially unsaturated or        maximally unsaturated heteromonocyclic or heterobicyclic ring        containing 1, 2, 3 or 4 heteroatoms or heteroatom groups        selected from N, O, S, NO, SO and SO₂, as ring members, where        the heteromono- or heterobicyclic ring may be substituted by one        or more, preferably 1, 2 or 3, in particular 1, radicals R¹;

-   R^(3a), R^(3b) are each independently selected from the group    consisting of hydrogen, halogen, —CO₂R^(3d), hydroxyl, C₁-C₃-alkyl,    C₁-C₃-haloalkyl, C₂-C₃-alkenyl, C₂-C₃-alkynyl, C₁-C₃-alkoxy,    C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio,    C₁-C₃-alkylsulfonyl and C₁-C₃-haloalkylsulfonyl; or    -   R^(3a) and R^(3b) together form a group ═O, ═C(R^(3c))₂, ═NOH or        ═NOCH₃;

-   each R^(3c) is independently selected from the group consisting of    hydrogen, halogen, CH₃ and CF₃;

-   R^(3d) is selected from the group consisting of hydrogen,    C₁-C₆-alkyl and C₁-C₃-alkyloxy-C₁-C₃-alkyl-;

-   each R⁴ is independently selected from the group consisting of    hydrogen, halogen, cyano, azido, nitro, —SCN, —SF₅, C₁-C₆-alkyl    which may be partially or fully halogenated and/or may be    substituted by one or more, preferably 1, 2 or 3, in particular 1,    radicals R⁸, C₃-C₈-cycloalkyl which may be partially or fully    halogenated and/or may be substituted by one or more, preferably 1,    2 or 3, in particular 1, radicals R⁸, C₂-C₆-alkenyl which may be    partially or fully halogenated and/or may be substituted by one or    more, preferably 1, 2 or 3, in particular 1, radicals R⁸,    C₂-C₆-alkynyl which may be partially or fully halogenated and/or may    be substituted by one or more, preferably 1, 2 or 3, in particular    1, radicals R⁸,    -   —Si(R¹²)₃, —OR⁹, —S(O)_(n)R⁹, —NR^(10a)R^(10b)    -   phenyl which may be substituted by 1, 2, 3, 4 or 5, preferably        1, 2 or 3, in particular 1, radicals R¹¹, and a 3-, 4-, 5-, 6-        7-, 8-, 9- or 10-membered saturated, partially unsaturated or        maximally unsaturated heteromonocyclic or heterobicyclic ring        containing 1, 2, 3 or 4 heteroatoms or heteroatom groups        selected from N, O, S, NO, SO and SO₂, as ring members, where        the heteromonocyclic or heterobicyclic ring may be substituted        by one or more, preferably 1, 2 or 3, in particular 1, radicals        R¹¹;

-   each R⁵ is independently selected from the group consisting of    hydrogen, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl,    C₂-C₁₀-alkynyl, wherein the four last-mentioned aliphatic and    cycloaliphatic radicals may be partially or fully halogenated and/or    may be substituted with one or more, preferably 1, 2 or 3, in    particular 1, substituents R⁸, and    -   —S(O)_(n)R⁹,

-   each R⁶ is independently selected from the group consisting of    hydrogen, cyano, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl,    C₂-C₁₀-alkynyl, wherein the four last-mentioned aliphatic and    cycloaliphatic radicals may be partially or fully halogenated and/or    may be substituted by one or more, preferably 1, 2 or 3, in    particular 1, substituents R⁸,    -   —OR⁹, —NR^(10a)R^(10b), —S(O)_(n)R⁹,        —C(═O)NR^(10a)N(R^(10a)R^(10b)), —Si(R¹²)₃, —C(═O)R⁸, phenyl        which may be substituted with 1, 2, 3, 4, or 5, preferably 1, 2        or 3, in particular 1, substituents R¹¹, and    -   a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially        unsaturated or maximally unsaturated heteromonocyclic or        heterobicyclic ring containing 1, 2, 3 or 4 heteroatoms or        heteroatom groups independently selected from N, O, S, NO, SO        and SO₂, as ring members, where the heteromonocyclic or        heterobicyclic ring may be substituted with one or more,        preferably 1, 2 or 3, in particular 1, substituents R¹¹;    -   or R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated,        partially unsaturated or maximally unsaturated heterocyclic        ring, where the ring may further contain 1, 2, 3 or 4        heteroatoms or heteroatom-containing groups selected from O, S,        N, SO, SO₂, C═O and C═S as ring members, wherein the        heterocyclic ring may be substituted with 1, 2, 3, 4 or 5,        preferably 1, 2 or 3, in particular 1, substituents        independently selected from the group consisting of halogen,        cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,        C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, wherein the        aliphatic or cycloaliphatic moieties in the twelve        last-mentioned radicals may be substituted by one or more,        preferably 1, 2 or 3, in particular 1, radicals R⁸, and phenyl        which may be substituted with 1, 2, 3, 4 or 5 substituents R¹¹;    -   or R⁵ and R⁶ together form a group ═C(R⁸)₂, ═S(O)_(m)(R⁹)₂,        ═NR^(10a) or ═NOR⁹;

-   R^(7a), R^(7b) are each independently selected from the group    consisting of hydrogen, halogen, cyano, C₁-C₆-alkyl,    C₃-C₈-cycloalkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl, wherein the four    last-mentioned aliphatic and cycloaliphatic radicals may be    partially or fully halogenated and/or may be substituted by one or    more, preferably 1, 2 or 3, in particular 1, radicals R⁸;

-   each R⁸ is independently selected from the group consisting of    cyano, azido, nitro, —SCN, —SF₅, C₃-C₈-cycloalkyl,    C₃-C₈-halocycloalkyl, where the cycloaliphatic moieties in the two    last-mentioned radicals may be substituted by one or more,    preferably 1, 2 or 3, in particular 1, radicals R¹³;    -   —Si(R¹²)₃, —OR⁹, —OSO₂R⁹, —S(O)_(n)R⁹, —N(R^(10a))R^(10b),        —C(═O)N(R^(10a))R^(10b), —C(═S)N(R^(10a))R^(10b), —C(═O)OR⁹,        -   phenyl, optionally substituted with 1, 2, 3, 4 or 5,            preferably 1, 2 or 3, in particular 1, substituents R¹⁶, and        -   a 3-, 4-, 5-, 6- or 7-membered saturated, partially            unsaturated or maximally unsaturated heterocyclic ring            comprising 1, 2 or 3 heteroatoms or heteroatom groups            selected from N, O, S, NO, SO and SO₂, as ring members,            where the heterocyclic ring is optionally substituted with            one or more, preferably 1, 2 or 3, in particular 1,            substituents R¹⁶,    -   or    -   two R⁸ present on the same carbon atom of an alkyl, alkenyl,        alkynyl or cycloalkyl group together form a group ═O, ═C(R¹³)₂;        ═S; ═S(O)_(m)(R¹⁵)₂, ═S(O)_(m)R¹⁵N(R^(14a))R^(14b), ═NR^(10a),        ═NOR⁹; or ═NN(R^(10a))R^(10b);    -   or    -   two radicals R⁸, together with the carbon atoms of an alkyl,        alkenyl, alkynyl or cycloalkyl group which they are bonded to,        form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially        unsaturated carbocyclic or heterocyclic ring, where the        heterocyclic ring comprises 1, 2, 3 or 4 heteroatoms or        heteroatom groups independently selected from N, O, S, NO, SO        and SO₂, as ring members, and where the carbocyclic or        heterocyclic ring is optionally substituted with one or more,        preferably 1, 2 or 3, in particular 1, substituents R¹⁶; and    -   R⁸ as a substituent on a cycloalkyl ring is additionally        selected from the group consisting of C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl        and C₂-C₆-haloalkynyl, where the aliphatic moieties in these six        radicals may be substituted by one or more, preferably 1, 2 or        3, in particular 1, radicals R¹³; and    -   R⁸ in the groups —C(═NR⁶)R⁸, —C(═O)R⁸ and ═C(R⁸)₂ is        additionally selected from the group consisting of hydrogen,        halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl and C₂-C₆-haloalkynyl, where        the aliphatic moieties in the six last-mentioned radicals may be        substituted by one or more, preferably 1, 2 or 3, in particular        1, radicals R¹³;

-   each R⁹ is independently selected from the group consisting of    hydrogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl,    C₃-C₈-cycloalkyl-C₁-C₄-alkyl-, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,    C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, where the    aliphatic and cycloaliphatic moieties in the nine last-mentioned    radicals may be substituted by one or more, preferably 1, 2 or 3, in    particular 1, radicals R¹³    -   —C₁-C₆-alkyl-C(═O)OR¹⁵, —C₁-C₆-alkyl-C(═O)N(R^(14a))R^(14b),    -   —C₁-C₆-alkyl-C(═S)N(R^(14a))R^(14b),        —C₁-C₆-alkyl-C(═NR¹⁴)N(R^(14a))R^(14b),    -   —Si(R¹²)₃, —S(O)_(n)R¹⁵, —S(O)_(n)N(R^(14a))R^(14b),        —N(R^(10a))R^(10b), —N═C(R¹³)₂, —C(═O)R¹³,        —C(═O)N(R^(14a))R^(14b), —C(═S)N(R^(14a))R^(14b), —C(═O)OR¹⁵,    -   phenyl, optionally substituted with 1, 2, 3, 4 or 5, preferably        1, 2 or 3, in particular 1, substituents R¹⁶; and    -   a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated        or maximally unsaturated heterocyclic ring comprising 1, 2 or 3        heteroatoms or heteroatom groups selected from N, O, S, NO, SO        and SO₂, as ring members, where the heterocyclic ring is        optionally substituted with one or more, preferably 1, 2 or 3,        in particular 1, substituents R¹⁶; and    -   R⁹ in the groups —S(O)_(n)R⁹ and —OSO₂R⁹ is additionally        selected from the group consisting of C₁-C₆-alkoxy and        C₁-C₆-haloalkoxy;

-   R^(10a), R^(10b) are selected independently from one another from    the group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,    C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, where the    aliphatic and cycloaliphatic moieties in the eight last-mentioned    radicals may be substituted by one or more radicals R¹³;    C₁-C₆-alkyl-C(═O)OR¹⁵, C₁-C₆-alkyl-C(═O)N(R^(14a))R^(14b),    —C₁-C₆-alkyl-C(═S)N(R^(14a))R^(14b),    —C₁-C₆-alkyl-C(═NR¹⁴)N(R^(14a))R^(14b), C₁-C₆-alkoxy,    C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,    -   —S(O)_(n)R¹⁵, —S(O)_(n)N(R^(14a))R^(14b), —C(═O)R¹³, —C(═O)OR¹⁵,        —C(═O)N(R^(14a))R^(14b), —C(═S)R¹³, —C(═S)SR¹⁵,        —C(═S)N(R^(14a))R^(14b), —C(═NR¹⁴)R¹³;    -   phenyl, optionally substituted with 1, 2, 3 or 4, preferably 1,        2 or 3, in particular 1, substituents R¹⁶; and    -   a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated        or maximally unsaturated heterocyclic ring comprising 1, 2, 3 or        4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO        and SO₂, as ring members, where the heterocyclic ring is        optionally substituted with one or more, preferably 1, 2 or 3,        in particular 1, substituents R¹⁶;    -   or    -   R^(10a) and R^(10b) form together with the nitrogen atom they        are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated,        partially unsaturated or maximally unsaturated heterocyclic        ring, wherein the heterocyclic ring may additionally contain one        or two heteroatoms or heteroatom groups selected from N, O, S,        NO, SO and SO₂, as ring members, where the heterocyclic ring        optionally carries one or more, preferably 1, 2 or 3, in        particular 1, substituents selected from halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl,        C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,        C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl, optionally substituted        with 1, 2, 3, 4 or 5, preferably 1, 2 or 3, in particular 1,        substituents R¹⁶, and a 3-, 4-, 5-, 6,- or 7-membered saturated,        partially unsaturated or maximally unsaturated heterocyclic ring        comprising 1, 2 or 3 heteroatoms or heteroatom groups selected        from N, O, S, NO, SO and SO₂, as ring members, where the        heterocyclic ring optionally carries one or more, preferably 1,        2 or 3, in particular 1, substituents R¹⁶; or R^(10a) and        R^(10b) together form a group ═C(R¹³)₂, ═S(O)_(m)(R¹⁵)₂,        ═S(O)_(m)R¹⁵N(R^(14a))R^(14b), ═NR¹⁴ or ═NOR¹⁵;

-   R¹¹ is independently selected from the group consisting of halogen,    cyano, azido, nitro, SCN, SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,    C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the four last-mentioned    aliphatic and cycloaliphatic radicals may be partially or fully    halogenated and/or may be substituted with one or more, preferably    1, 2 or 3, in particular 1, radicals R⁸,    -   —OR⁹, —NR^(10a)R^(10b), —S(O)_(n)R⁹, —Si(R¹²)₃;    -   phenyl, optionally substituted with 1, 2, 3, 4, or 5, preferably        1, 2 or 3, in particular 1, substituents selected independently        from R¹⁶; and    -   a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated        or maximally unsaturated aromatic heterocyclic ring comprising        1, 2, 3 or 4 heteroatoms or heteroatom groups selected from N,        O, S, NO, SO and SO₂, as ring members, where the heterocyclic        ring is optionally substituted with one or more, preferably 1, 2        or 3, in particular 1, substituents selected independently from        R¹⁶;    -   or two R¹¹ present on the same ring carbon atom of an        unsaturated or partially unsaturated heterocyclic ring may        together form a group ═O, ═C(R¹³)₂; ═S; ═S(O)_(m)(R¹⁵)₂;        ═S(O)_(m)R¹⁵N(R^(14a))R^(14b), ═NR¹⁴, ═NOR¹⁵, or        ═NN(R^(14a))R^(14b);    -   or two R¹¹ bound on adjacent ring atoms form together with the        ring atoms to which they are bound a saturated 3-, 4-, 5-, 6-,        7-, 8- or 9-membered ring, wherein the ring may contain 1 or 2        heteroatoms or heteroatom groups selected from O, S, N, NR¹⁴,        NO, SO and SO₂ and/or 1 or 2 groups selected from C═O, C═S and        C═NR¹⁴ as ring members, and wherein the ring may be substituted        by one or more, preferably 1, 2 or 3, in particular 1, radicals        selected from the group consisting of halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl,        C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,        C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl which may be        substituted by 1, 2, 3, 4 or 5, preferably 1, 2 or 3, in        particular 1, radicals R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered        saturated, partially unsaturated or maximally unsaturated        heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom        groups selected from N, O, S, NO, SO and SO₂, as ring members,        where the heterocyclic ring may be substituted by one or more,        preferably 1, 2 or 3, in particular 1, radicals R¹⁶;

-   each R¹² is independently selected from the group consisting of    hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,    C₁-C₆-haloalkoxy, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,    C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,    C₁-C₆-haloalkoxy-C₁-C₆-alkyl, and    -   phenyl, optionally substituted with 1, 2, 3, 4, or 5, preferably        1, 2 or 3, preferably 1 or 2, in particular 1, substituents R¹⁶;

-   each R¹³ is independently selected from the group consisting of    cyano, nitro, —OH, —SH, —SCN, —SF₅, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,    C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkylsulfonyl, trimethylsilyl, triethylsilyl,    tert-butyldimethylsilyl, C₃-C₈-cycloalkyl which may be    unsubstituted, partially or fully halogenated and/or may carry 1 or    2, in particular 1, radicals selected from C₁-C₄-alkyl,    C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and oxo; phenyl,    benzyl, phenoxy, where the phenyl moiety in the three last-mentioned    radicals may be unsubstituted, partially or fully halogenated and/or    carry 1, 2, 3, 4 or 5, preferably 1, 2 or 3, more preferably 1 or 2,    in particular 1, substituents R¹⁶; and a 3-, 4-, 5-, 6- or    7-membered saturated, partially unsaturated or maximally unsaturated    heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom    groups selected from N, O, S, NO, SO and SO₂, as ring members, where    the heterocyclic ring may be substituted by 1, 2 or 3, preferably 1    or 2, in particular 1, substituents R¹⁶;    -   or    -   two R¹³ present on the same carbon atom (of an alkyl, alkenyl,        alkynyl or cycloalkyl group) may together be ═O,        ═CH(C₁-C₄-alkyl), ═C(C₁-C₄-alkyl)C₁-C₄-alkyl, ═N(C₁-C₆-alkyl) or        ═NO(C₁-C₆-alkyl);    -   and    -   R¹³ as a substituent on a cycloalkyl ring is additionally        selected from the group consisting of C₁-C₆-alkyl, C₂-C₆-alkenyl        and C₂-C₆-alkynyl, wherein the three last-mentioned aliphatic        radicals may be unsubstituted, partially or fully halogenated        and/or may carry 1 or 2, in particular 1, substituents selected        from CN, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and        oxo;    -   and    -   R¹³ in the groups ═C(R¹³)₂, —N═C(R¹³)₂, —C(═O)R¹³, —C(═S)R¹³ and    -   —C(═NR¹⁴)R¹³ is additionally selected from the group consisting        of hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl and        C₂-C₆-alkynyl, wherein the three last-mentioned aliphatic        radicals may be unsubstituted, partially or fully halogenated        and/or may carry 1 or 2, in particular 1, radicals selected from        CN, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and oxo;

-   each R¹⁴ is independently selected from the group consisting of    hydrogen, cyano, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,    C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl,    C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, trimethylsilyl,    triethylsilyl, tert-butyldimethylsilyl,    -   C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the three        last-mentioned aliphatic radicals may be unsubstituted,        partially or fully halogenated and/or may carry 1 or 2, in        particular 1, radicals selected from CN, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,        C₁-C₄-alkylsulfonyl, C₃-C₄-cycloalkyl which may be substituted        by 1 or 2, in particular 1, substituents selected from halogen        and cyano; and oxo;    -   C₃-C₈-cycloalkyl which may be unsubstituted, partially or fully        halogenated and/or may carry 1 or 2, in particular 1, radicals        selected from C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl,        C₃-C₄-cycloalkyl, C₃-C₄-cycloalkyl-C₁-C₄-alkyl-, where the        cycloalkyl moiety in the two last-mentioned radicals may be        substituted by 1 or 2, in particular 1, substituents selected        from halogen and cyano; and oxo;    -   phenyl, benzyl, pyridyl, phenoxy, wherein the cyclic moieties in        the four last-mentioned radicals may be unsubstituted and/or        carry 1, 2 or 3, in particular 1, substituents selected from        halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy and (C₁-C₆-alkoxy)carbonyl; and a 3-, 4-, 5- or        6-membered saturated, partially unsaturated or maximally        unsaturated heterocyclic ring comprising 1 or 2 heteroatoms or        heteroatom groups selected from N, O, S, NO, SO and SO₂, as ring        members, where the heterocyclic ring is optionally substituted        with one or more substituents R¹⁶;

-   R^(14a) and R^(14b), independently of each other, have one of the    meanings given for R¹⁴;    -   or    -   R^(14a) and R^(14b), together with the nitrogen atom to which        they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated,        partially unsaturated or maximally unsaturated heterocyclic        ring, wherein the heterocyclic ring may additionally contain 1        or 2 heteroatoms or heteroatom groups selected from N, O, S, NO,        SO and SO₂, as ring members, where the heterocyclic ring        optionally carries one or more, preferably 1, 2 or 3, in        particular 1, substitutents selected from halogen, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;    -   or    -   R^(14a) and R¹⁴ or R^(14b) and R¹⁴, together with the nitrogen        atoms to which they are bound in the group        —C(═NR¹⁴)N(R^(14a))R^(14b), form a 3-, 4-, 5-, 6- or 7-membered        partially unsaturated or maximally unsaturated heterocyclic        ring, wherein the heterocyclic ring may additionally contain 1        or 2 heteroatoms or heteroatom groups selected from N, O, S, NO,        SO and SO₂, as ring members, where the heterocyclic ring        optionally carries one or more, preferably 1, 2 or 3, in        particular 1, substituents selected from halogen,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

-   each R¹⁵ is independently selected from the group consisting of    hydrogen, cyano, trimethylsilyl, triethylsilyl,    tert-butyldimethylsilyl,    -   C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the three        last-mentioned aliphatic radicals may be unsubstituted,        partially or fully halogenated and/or may carry 1 or 2, in        particular 1, radicals selected from C₃-C₄-cycloalkyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,        C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl and oxo;        C₃-C₈-cycloalkyl which may be unsubstituted, partially or fully        halogenated and/or may carry 1 or 2, in particular 1, radicals        selected from C₁-C₄-alkyl, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,        C₁-C₄-alkylsulfonyl and oxo;    -   phenyl, benzyl, pyridyl and phenoxy, wherein the four        last-mentioned radicals may be unsubstituted, partially or fully        halogenated and/or carry 1, 2 or 3, preferably 1 or 2 in        particular 1, substituents selected from C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and        (C₁-C₆-alkoxy)carbonyl;

-   each R¹⁶ is independently selected from the group consisting of    halogen, nitro, cyano, —OH, —SH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,    C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkylsulfonyl, trimethylsilyl, triethylsilyl,    tert-butyldimethylsilyl;    -   C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the three        last-mentioned aliphatic radicals may be unsubstituted,        partially or fully halogenated and/or may carry 1 or 2, in        particular 1, radicals selected from C₃-C₄-cycloalkyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and oxo;    -   C₃-C₈-cycloalkyl which may be unsubstituted, partially or fully        halogenated and/or may carry 1 or 2, in particular 1, radicals        selected from C₁-C₄-alkyl, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy and oxo;    -   phenyl, benzyl, pyridyl and phenoxy, wherein the four last        mentioned radicals may be unsubstituted, partially or fully        halogenated and/or carry 1, 2 or 3, in particular 1,        substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and (C₁-C₆-alkoxy)carbonyl;    -   or    -   two R¹⁶ present together on the same atom of an unsaturated or        partially unsaturated ring may be ═O, ═S, ═N(C₁-C₆-alkyl),        ═NO(C₁-C₆-alkyl), ═CH(C₁-C₄-alkyl) or        ═C(C₁-C₄-alkyl)C₁-C₄-alkyl;    -   or    -   two R¹⁶ on two adjacent carbon atoms form together with the        carbon atoms they are bonded to a 4-, 5-, 6-, 7- or 8-membered        saturated, partially unsaturated or maximally unsaturated ring,        wherein the ring may contain 1 or 2 heteroatoms or heteroatom        groups selected from N, O, S, NO, SO and SO₂, as ring members,        and wherein the ring optionally carries one or more, preferably        1, 2 or 3, in particular 1, substituents selected from halogen,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

-   each n is independently 0, 1 or 2; and

-   each m is independently 0 or 1;    and the N-oxides, stereoisomers and agriculturally or veterinarily    acceptable salts thereof.

-   The present invention also provides an agricultural composition    comprising at least one compound of the formula I as defined herein    and/or an agriculturally acceptable salt thereof and at least one    liquid or solid carrier.

The present invention also provides a veterinary composition comprisingat least one compound of the formula I as defined herein and/or aveterinarily acceptable salt thereof and at least one liquid or solidcarrier.

The present invention also provides a method for controllinginvertebrate pests which method comprises treating the pests, their foodsupply, their habitat or their breeding ground or a cultivated plant,plant propagation materials (such as seed), soil, area, material orenvironment in which the pests are growing or may grow, or thematerials, cultivated plants, plant propagation materials (such asseed), soils, surfaces or spaces to be protected from pest attack orinfestation with a pesticidally effective amount of a compound offormula I or a salt thereof as defined herein.

The present invention also relates to plant propagation material, inparticular seed, comprising at least one compound of formula I and/or anagriculturally acceptable salt thereof as defined herein.

The present invention further relates to a method for treating orprotecting an animal from infestation or infection by parasites whichcomprises bringing the animal in contact with a parasiticidallyeffective amount of a compound of the formula I or a veterinarilyacceptable salt thereof as defined herein. Bringing the animal incontact with the compound I, its salt or the veterinary composition ofthe invention means applying or administering it to the animal.

The term “steroisomers” encompasses both optical isomers, such asenantiomers or diastereomers, the latter existing due to more than onecenter of chirality in the molecule, as well as geometrical isomers(cis/trans isomers).

Depending on the substitution pattern, the compounds of the formula Imay have one or more centers of chirality, in which case they arepresent as mixtures of enantiomers or diastereomers. One center ofchirality is the carbon ring atom of the isothiazoline ring carryingradical R¹. The invention provides both the pure enantiomers ordiastereomers and their mixtures and the use according to the inventionof the pure enantiomers or diastereomers of the compound I or itsmixtures. Suitable compounds of the formula I also include all possiblegeometrical stereoisomers (cis/trans isomers) and mixtures thereof.

The term N-oxides relates to a form of compounds I in which at least onenitrogen atom is present in oxidized form (as NO).

The compounds of the present invention may be amorphous or may exist inone or more different crystalline states (polymorphs) which may have adifferent macroscopic properties such as stability or show differentbiological properties such as activities. The present invention includesboth amorphous and crystalline compounds of the formula I, mixtures ofdifferent crystalline states of the respective compound I, as well asamorphous or crystalline salts thereof.

Salts of the compounds of the formula I are preferably agriculturallyand veterinarily acceptable salts. They can be formed in a customarymethod, e.g. by reacting the compound with an acid of the anion inquestion if the compound of formula I has a basic functionality or byreacting an acidic compound of formula I with a suitable base.

Suitable agriculturally acceptable salts are especially the salts ofthose cations or the acid addition salts of those acids whose cationsand anions, respectively, do not have any adverse effect on the actionof the compounds according to the present invention. Suitable cationsare in particular the ions of the alkali metals, preferably lithium,sodium and potassium, of the alkaline earth metals, preferably calcium,magnesium and barium, and of the transition metals, preferablymanganese, copper, zinc and iron, and also ammonium (NH⁴⁺) andsubstituted ammonium in which one to four of the hydrogen atoms arereplaced by C₁-C₄-alkyl, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl orbenzyl. Examples of substituted ammonium ions comprise methylammonium,isopropylammonium, dimethylammonium, diisopropylammonium,trimethylammonium, tetramethylammonium, tetraethylammonium,tetrabutylammonium, 2-hydroxyethylammonium,2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium,benzyltrimethylammonium and benzl-triethylammonium, furthermorephosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium,and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, phosphate, nitrate, hydrogen carbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate, and the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate. They can be formed by reacting a compound of formulae I withan acid of the corresponding anion, preferably of hydrochloric acid,hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

By the term “veterinarily acceptable salts” is meant salts of thosecations or anions which are known and accepted in the art for theformation of salts for veterinary use. Suitable acid addition salts,e.g. formed by compounds of formula I containing a basic nitrogen atom,e.g. an amino group, include salts with inorganic acids, for examplehydrochlorids, sulphates, phosphates, and nitrates and salts of organicacids for example acetic acid, maleic acid, dimaleic acid, fumaric acid,difumaric acid, methane sulfenic acid, methane sulfonic acid, andsuccinic acid.

The term “invertebrate pest” as used herein encompasses animalpopulations, such as insects, arachnids and nematodes, which may attackplants, thereby causing substantial damage to the plants attacked, aswell as ectoparasites which may infest animals, in particular warmblooded animals such as e.g. mammals or birds, or other higher animalssuch as reptiles, amphibians or fish, thereby causing substantial damageto the animals infested.

The term “plant propagation material” is to be understood to denote allthe generative parts of the plant such as seeds and vegetative plantmaterial such as cuttings and tubers (e.g. potatoes), which can be usedfor the multiplication of the plant. This includes seeds, roots, fruits,tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants,including seedlings and young plants, which are to be transplanted aftergermination or after emergence from soil. The plant propagationmaterials may be treated prophylactically with a plant protectioncompound either at or before planting or transplanting. Said youngplants may also be protected before transplantation by a total orpartial treatment by immersion or pouring.

The term “plants” comprises any types of plants including“non-cultivated plants” and in particular “cultivated plants”.

The term “non-cultivated plants” refers to any wild type species orrelated species or related genera of a cultivated plant.

The term “cultivated plants” is to be understood as including plantswhich have been modified by breeding, mutagenesis or genetic engineeringincluding but not limiting to agricultural biotech products on themarket or in development (cf.http://www.bio.org/speeches/pubs/er/agri_products.asp). Geneticallymodified plants are plants, which genetic material has been so modifiedby the use of recombinant DNA techniques that under naturalcircumstances cannot readily be obtained by cross breeding, mutations ornatural recombination. Typically, one or more genes have been integratedinto the genetic material of a genetically modified plant in order toimprove certain properties of the plant. Such genetic modifications alsoinclude but are not limited to targeted post-translational modificationof protein(s), oligo- or polypeptides e.g. by glycosylation or polymeradditions such as prenylated, acetylated or farnesylated moieties or PEGmoieties.

Plants that have been modified by breeding, mutagenesis or geneticengineering, e.g. have been rendered tolerant to applications ofspecific classes of herbicides, such as auxin herbicides such as dicambaor 2,4-D; bleacher herbicides such as hydroxyl-phenylpyruvatedioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors;acetolactate synthase (ALS) inhibitors such as sulfonyl ureas orimidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS)inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitorssuch as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipidbiosynthesis inhibitors such as acetyl CoA carboxylase (ACCase)inhibitors; or oxynil (i.e. bromoxynil or ioxynil) herbicides as aresult of conventional methods of breeding or genetic engineering.Furthermore, plants have been made resistant to multiple classes ofherbicides through multiple genetic modifications, such as resistance toboth glyphosate and glufosinate or to both glyphosate and a herbicidefrom another class such as ALS inhibitors, HPPD inhibitors, auxinherbicides, or ACCase inhibitors. These herbicide resistancetechnologies are e.g. described in Pest Managem. Sci. 61, 2005, 246; 61,2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326;64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58,2007, 708; Science 316, 2007, 1185; and references quoted therein.Several cultivated plants have been rendered tolerant to herbicides byconventional methods of breeding (mutagenesis), e.g. Clearfield® summerrape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e.g.imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant tosulfonyl ureas, e.g. tribenuron. Genetic engineering methods have beenused to render cultivated plants such as soybean, cotton, corn, beetsand rape, tolerant to herbicides such as glyphosate and glufosinate,some of which are commercially available under the trade namesRoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance®(imidazolinone tolerant, BASF SE, Germany) and LibertyLink®(glufosinate-tolerant, Bayer CropScience, Germany).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more insecticidal proteins,especially those known from the bacterial genus Bacillus, particularlyfrom Bacillus thuringiensis, such as δ-endotoxins, e.g. CryIA(b),CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c;vegetative insecticidal proteins (VIP), e.g. VIP1, VIP2, VIP3 or VIP3A;insecticidal proteins of bacteria colonizing nematodes, e.g.Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, suchas scorpion toxins, arachnid toxins, wasp toxins, or otherinsect-specific neurotoxins; toxins produced by fungi, suchStreptomycetes toxins, plant lectins, such as pea or barley lectins;agglutinins; proteinase inhibitors, such as trypsin inhibitors, serineprotease inhibitors, patatin, cystatin or papain inhibitors;ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin,luffin, saporin or bryodin; steroid metabolism enzymes, such as3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase,cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ionchannel blockers, such as blockers of sodium or calcium channels;juvenile hormone esterase; diuretic hormone receptors (helicokininreceptors); stilben synthase, bibenzyl synthase, chitinases orglucanases. In the context of the present invention these insecticidalproteins or toxins are to be understood expressly also as pre-toxins,hybrid proteins, truncated or otherwise modified proteins. Hybridproteins are characterized by a new combination of protein domains,(see, e.g. WO 02/015701). Further examples of such toxins or geneticallymodified plants capable of synthesizing such toxins are disclosed, e.g.,in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878,WO 03/18810 und WO 03/52073. The methods for producing such geneticallymodified plants are generally known to the person skilled in the art andare described, e.g. in the publications mentioned above. Theseinsecticidal proteins contained in the genetically modified plantsimpart to the plants producing these proteins tolerance to harmful pestsfrom all taxonomic groups of athropods, especially to beetles(Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) andto nematodes (Nematoda). Genetically modified plants capable tosynthesize one or more insecticidal proteins are, e.g., described in thepublications mentioned above, and some of which are commerciallyavailable such as YieldGard® (corn cultivars producing the Cry1Abtoxin), YieldGard® Plus (corn cultivars producing Cry1Ab and Cry3Bb1toxins), Starlink® (corn cultivars producing the Cry9c toxin),Herculex®RW (corn cultivars producing Cry34Ab1, Cry35Ab1 and the enzymePhosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cottoncultivars producing the Cry1Ac toxin), Bollgard® I (cotton cultivarsproducing the Cry1Ac toxin), Bollgard® II (cotton cultivars producingCry1Ac and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing aVIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin);BtXtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e.g.Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivarsproducing the Cry1Ab toxin and PAT enzyme), MIR604 from Syngenta SeedsSAS, France (corn cultivars producing a modified version of the Cry3Atoxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium(corn cultivars producing the Cry3Bb1 toxin), IPC 531 from MonsantoEurope S.A., Belgium (cotton cultivars producing a modified version ofthe Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium(corn cultivars producing the CryIF toxin and PAT enzyme).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe resistance or tolerance of those plants to bacterial, viral orfungal pathogens. Examples of such proteins are the so-called“pathogenesis-related proteins” (PR proteins, see, e.g. EP-A 392 225),plant disease resistance genes (e.g. potato cultivars, which expressresistance genes acting against Phytophthora infestans derived from themexican wild potato Solanum bulbocastanum) or T4-lysozym (e.g. potatocultivars capable of synthesizing these proteins with increasedresistance against bacteria such as Erwinia amylvora). The methods forproducing such genetically modified plants are generally known to theperson skilled in the art and are described, e.g. in the publicationsmentioned above.

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe productivity (e.g. bio mass production, grain yield, starch content,oil content or protein content), tolerance to drought, salinity or othergrowth-limiting environmental factors or tolerance to pests and fungal,bacterial or viral pathogens of those plants.

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of substances of content ornew substances of content, specifically to improve human or animalnutrition, e.g. oil crops that produce health-promoting long-chainomega-3 fatty acids or unsaturated omega-9 fatty acids (e.g. Nexera®rape, DOW Agro Sciences, Canada).

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of substances of content ornew substances of content, specifically to improve raw materialproduction, e.g. potatoes that produce increased amounts of amylopectin(e.g. Amflora® potato, BASF SE, Germany).

The organic moieties mentioned in the above definitions of the variablesare—like the term halogen—collective terms for individual listings ofthe individual group members.

The prefix C_(n)-C_(m) indicates in each case the possible number ofcarbon atoms in the group.

The term halogen denotes in each case fluorine, bromine, chlorine oriodine, in particular fluorine, chlorine or bromine.

The term “alkyl” as used herein and in the alkyl moieties of alkoxy,alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyland the like refers to saturated straight-chain or branched hydrocarbonradicals having 1 to 2 (“C₁-C₂-alkyl”), 1 to 3 (“C₁-C₃-alkyl”), 1 to 4(“C₁-C₄-alkyl”), 1 to 6 (“C₁-C₆-alkyl”), 1 to 8 (“C₁-C₈-alkyl”) or 1 to10 (“C₁-C₁₀-alkyl”) carbon atoms. C₁-C₂-Alkyl is methyl or ethyl.C₁-C₃-Alkyl is additionally propyl and isopropyl. C₁-C₄-Alkyl isadditionally butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl(isobutyl) or 1,1-dimethylethyl (tert-butyl). C₁-C₆-Alkyl isadditionally also, for example, pentyl, 1-methylbutyl, 2-methylbutyl,3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl,1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl,3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or1-ethyl-2-methylpropyl. C₁-C₈-Alkyl is additionally also, for example,heptyl, octyl, 2-ethylhexyl and positional isomers thereof. C₁-C₁₀-Alkylis additionally also, for example, nonyl, decyl and positional isomersthereof.

The term “haloalkyl” as used herein, which is also expressed as “alkylwhich is partially or fully halogenated”, refers to straight-chain orbranched alkyl groups having 1 to 2 (“C₁-C₂-haloalkyl”), 1 to 3(“C₁-C₃-haloalkyl”), 1 to 4 (“C₁-C₄-haloalkyl”), 1 to 6(“C₁-C₆-haloalkyl”), 1 to 8 (“C₁-C₈-haloalkyl”) or 1 to 10(“C₁-C₁₀-haloalkyl”) carbon atoms (as mentioned above), where some orall of the hydrogen atoms in these groups are replaced by halogen atomsas mentioned above: in particular C₁-C₂-haloalkyl, such as chloromethyl,bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl,1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl.C₁-C₃-haloalkyl is additionally, for example, 1-fluoropropyl,2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl,1,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl,heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl and thelike. Examples for C₁-C₄-haloalkyl are, apart those mentioned forC₁-C₃-haloalkyl, 4-chlorobutyl and the like.

“Halomethyl” is methyl in which 1, 2 or 3 of the hydrogen atoms arereplaced by halogen atoms. Examples are bromomethyl, chloromethyl,fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl and the like.

The term “alkenyl” as used herein refers to monounsaturatedstraight-chain or branched hydrocarbon radicals having 2 to 3(“C₂-C₃-alkenyl”), 2 to 4 (“C₂-C₄-alkenyl”), 2 to 6 (“C₂-C₆-alkenyl”), 2to 8 (“C₂-C₈-alkenyl”) or 2 to 10 (“C₂-C₁₀-alkenyl”) carbon atoms and adouble bond in any position, for example C₂-C₃-alkenyl, such as ethenyl,1-propenyl, 2-propenyl or 1-methylethenyl; C₂-C₄-alkenyl, such asethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl,3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenylor 2-methyl-2-propenyl; C₂-C₆-alkenyl, such as ethenyl, 1-propenyl,2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl and the like,or C₂-C₁₀-alkenyl, such as the radicals mentioned for C₂-C₆-alkenyl andadditionally 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl,3-octenyl, 4-octenyl, 1-nonenyl, 2-nonenyl, 3-nonenyl, 4-nonenyl,1-decenyl, 2-decenyl, 3-decenyl, 4-decenyl, 5-decenyl and the positionalisomers thereof.

The term “haloalkenyl” as used herein, which is also expressed as“alkenyl which is partially or fully halogenated”, refers to unsaturatedstraight-chain or branched hydrocarbon radicals having 2 to 4(“C₂-C₄-haloalkenyl”), 2 to 6 (“C₂-C₆-haloalkenyl”), 2 to 8(“C₂-C₆-haloalkenyl”) or 2 to 10 (“C₂-C₁₀-haloalkenyl”) carbon atoms anda double bond in any position (as mentioned above), where some or all ofthe hydrogen atoms in these groups are replaced by halogen atoms asmentioned above, in particular fluorine, chlorine and bromine, forexample chlorovinyl, chloroallyl and the like.

The term “alkynyl” as used herein refers to straight-chain or branchedhydrocarbon groups having 2 to 3 (“C₂-C₃-alkynyl”), 2 to 4(“C₂-C₄-alkynyl”), 2 to 6 (“C₂-C₆-alkynyl”), 2 to 8 (“C₂-C₈-alkynyl”),or 2 to 10 (“C₂-C₁₀-alkynyl”) carbon atoms and one or two triple bondsin any position, for example C₂-C₃-alkynyl, such as ethynyl, 1-propynylor 2-propynyl; C₂-C₄-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl,1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like,C₂-C₆-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl,2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl,3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl,1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl,5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl,1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl,3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl,4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl,1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl,1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl,1-ethyl-1-methyl-2-propynyl and the like;

The term “haloalkynyl” as used herein, which is also expressed as“alkynyl which is partially or fully halogenated”, refers to unsaturatedstraight-chain or branched hydrocarbon radicals having 2 to 4(“C₂-C₄-haloalkynyl”), 3 to 4 (“C₃-C₄-haloalkynyl”), 2 to 6(“C₂-C₆-haloalkynyl”), 2 to 8 (“C₂-C₈-haloalkynyl”) or 2 to 10(“C₂-C₁₀-haloalkynyl”) carbon atoms and one or two triple bonds in anyposition (as mentioned above), where some or all of the hydrogen atomsin these groups are replaced by halogen atoms as mentioned above, inparticular fluorine, chlorine and bromine;

The term “cycloalkyl” as used herein refers to mono- or bi- orpolycyclic saturated hydrocarbon radicals having 3 to 8(“C₃-C₈-cycloalkyl”), in particular 3 to 6 carbon atoms(“C₃-C₆-cycloalkyl”). Examples of monocyclic radicals having 3 to 6carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl andcyclohexyl. Examples of monocyclic radicals having 3 to 8 carbon atomscomprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyland cyclooctyl. Examples of bicyclic radicals having 7 or 8 carbon atomscomprise bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyland bicyclo[3.2.1]octyl. Preferably, the term cycloalkyl denotes amonocyclic saturated hydrocarbon radical.

The term “halocycloalkyl” as used herein, which is also expressed as“cycloalkyl which is partially or fully halogenated”, refers to mono- orbi- or polycyclic saturated hydrocarbon groups having 3 to 8(“C₃-C₈-halocycloalkyl”) or preferably 3 to 6 (“C₃-C₆-halocycloalkyl”)carbon ring members (as mentioned above) in which some or all of thehydrogen atoms are replaced by halogen atoms as mentioned above, inparticular fluorine, chlorine and bromine.

The term “cycloalkyl-C₁-C₄-alkyl” refers to a C₃-C₈-cycloalkyl group(“C₃-C₈-cycloalkyl-C₁-C₄-alkyl”), preferably a C₃-C₆-cycloalkyl group(“C₃-C₆-cycloalkyl-C₁-C₄-alkyl”), more preferably a C₃-C₄-cycloalkylgroup (“C₃-C₄-cycloalkyl-C₁-C₄-alkyl”) as defined above (preferably amonocyclic cycloalkyl group) which is bound to the remainder of themolecule via a C₁-C₄-alkyl group, as defined above. Examples forC₃-C₄-cycloalkyl-C₁-C₄-alkyl are cyclopropylmethyl, cyclopropylethyl,cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl andcyclobutylpropyl, Examples for C₃-C₆-cycloalkyl-C₁-C₄-alkyl, apart thosementioned for C₃-C₄-cycloalkyl-C₁-C₄-alkyl, are cyclopentylmethyl,cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyland cyclohexylpropyl. Examples for C₃-C₈-cycloalkyl-C₁-C₄-alkyl, apartthose mentioned for C₃-C₆-cycloalkyl-C₁-C₄-alkyl, are cycloheptylmethyl,cycloheptylethyl, cyclooctylmethyl and the like.

The term “C₃-C₈-halocycloalkyl-C₁-C₄-alkyl” refers to aC₃-C₈-halocycloalkyl group as defined above which is bound to theremainder of the molecule via a C₁-C₄-alkyl group, as defined above.

The term “C₁-C₂-alkoxy” is a C₁-C₂-alkyl group, as defined above,attached via an oxygen atom. The term “C₁-C₃-alkoxy” is a C₁-C₃-alkylgroup, as defined above, attached via an oxygen atom. The term“C₁-C₄-alkoxy” is a C₁-C₄-alkyl group, as defined above, attached via anoxygen atom. The term “C₁-C₆-alkoxy” is a C₁-C₆-alkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₁₀-alkoxy” is aC₁-C₁₀-alkyl group, as defined above, attached via an oxygen atom.C₁-C₂-Alkoxy is methoxy or ethoxy. C₁-C₃-Alkoxy is additionally, forexample, n-propoxy and 1-methylethoxy (isopropoxy). C₁-C₄-Alkoxy isadditionally, for example, butoxy, 1-methylpropoxy (sec-butoxy),2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy).C₁-C₆-Alkoxy is additionally, for example, pentoxy, 1-methylbutoxy,2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or1-ethyl-2-methylpropoxy. C₁-C₈-Alkoxy is additionally, for example,heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.C₁-C₁₀-Alkoxy is additionally, for example, nonyloxy, decyloxy andpositional isomers thereof.

The term “C₁-C₂-haloalkoxy” is a C₁-C₂-haloalkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₃-haloalkoxy” is aC₁-C₃-haloalkyl group, as defined above, attached via an oxygen atom.The term “C₁-C₄-haloalkoxy” is a C₁-C₄-haloalkyl group, as definedabove, attached via an oxygen atom. The term “C₁-C₆-haloalkoxy” is aC₁-C₆-haloalkyl group, as defined above, attached via an oxygen atom.The term “C₁-C₁₀-haloalkoxy” is a C₁-C₁₀-haloalkyl group, as definedabove, attached via an oxygen atom. C₁-C₂-Haloalkoxy is, for example,OCH₂F, OCHF₂, OCF₃, OCH₂Cl, OCHCl₂, OCCl₃, chlorofluoromethoxy,dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy,2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy or OC₂F₅. C₁-C₃-Haloalkoxy is additionally, forexample, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy,2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy,3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH₂—C₂F₅, OCF₂—C₂F₅,1-(CH₂F)-2-fluoroethoxy, 1-(CH₂Cl)-2-chloroethoxy or1-(CH₂Br)-2-bromoethoxy. C₁-C₄-Haloalkoxy is additionally, for example,4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.C₁-C₆-Haloalkoxy is additionally, for example, 5-fluoropentoxy,5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy,6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy ordodecafluorohexoxy.

The term “C₁-C₄-alkoxy-C₁-C₄-alkyl” as used herein, refers to astraight-chain or branched alkyl group having 1 to 4 carbon atoms, asdefined above, where one hydrogen atom is replaced by a C₁-C₄-alkoxygroup, as defined above. The term “C₁-C₆-alkoxy-C₁-C₆-alkyl” as usedherein, refers to a straight-chain or branched alkyl group having 1 to 6carbon atoms, as defined above, where one hydrogen atom is replaced by aC₁-C₆-alkoxy group, as defined above. Examples are methoxymethyl,ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl,sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, 1-methoxyethyl,1-ethoxyethyl, 1-propoxyethyl, 1-isopropoxyethyl, 1-n-butoxyethyl,1-sec-butoxyethyl, 1-isobutoxyethyl, 1-tert-butoxyethyl, 2-methoxyethyl,2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n-butoxyethyl,2-sec-butoxyethyl, 2-isobutoxyethyl, 2-tert-butoxyethyl,1-methoxypropyl, 1-ethoxypropyl, 1-propoxypropyl, 1-isopropoxypropyl,1-n-butoxypropyl, 1-sec-butoxypropyl, 1-isobutoxypropyl,1-tert-butoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl,2-isopropoxypropyl, 2-n-butoxypropyl, 2-sec-butoxypropyl,2-isobutoxypropyl, 2-tert-butoxypropyl, 3-methoxypropyl, 3-ethoxypropyl,3-propoxypropyl, 3-isopropoxypropyl, 3-n-butoxypropyl,3-sec-butoxypropyl, 3-isobutoxypropyl, 3-tert-butoxypropyl and the like.

The term “C₁-C₆-alkoxy-methyl” as used herein, refers to methyl in whichone hydrogen atom is replaced by a C₁-C₆-alkoxy group, as defined above.Examples are methoxymethyl, ethoxymethyl, propoxymethyl,isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl,tert-butoxymethyl, pentyloxymethyl, hexyloxymethyl and the like.

C₁-C₆-Haloalkoxy-C₁-C₆-alkyl is a straight-chain or branched alkyl grouphaving from 1 to 6, especially 1 to 4 carbon atoms(═C₁-C₆-haloalkoxy-C₁-C₄-alkyl), wherein one of the hydrogen atoms isreplaced by a C₁-C₆-alkoxy group and wherein at least one, e.g. 1, 2, 3,4 or all of the remaining hydrogen atoms (either in the alkoxy moiety orin the alkyl moiety or in both) are replaced by halogen atoms.C₁-C₄-Haloalkoxy-C₁-C₄-alkyl is a straight-chain or branched alkyl grouphaving from 1 to 4 carbon atoms, wherein one of the hydrogen atoms isreplaced by a C₁-C₄-alkoxy group and wherein at least one, e.g. 1, 2, 3,4 or all of the remaining hydrogen atoms (either in the alkoxy moiety orin the alkyl moiety or in both) are replaced by halogen atoms. Examplesare difluoromethoxy-methyl (CHF₂OCH₂), trifluoromethoxymethyl,1-difluoromethoxyethyl, 1-trifluoromethoxyethyl, 2-difluoromethoxyethyl,2-trifluoromethoxyethyl, difluoromethoxy-methyl (CH₃OCF₂),1,1-difluoro-2-methoxyethyl, 2,2-difluoro-2-methoxyethyl and the like.

The term “C₁-C₂-alkylthio” is a C₁-C₂-alkyl group, as defined above,attached via a sulfur atom. The term “C₁-C₃-alkylthio” is a C₁-C₃-alkylgroup, as defined above, attached via a sulfur atom. The term“C₁-C₄-alkylthio” is a C₁-C₄-alkyl group, as defined above, attached viaa sulfur atom. The term “C₁-C₆-alkylthio” is a C₁-C₆-alkyl group, asdefined above, attached via a sulfur atom. The term “C₁-C₁₀-alkylthio”is a C₁-C₁₀-alkyl group, as defined above, attached via a sulfur atom.C₁-C₂-Alkylthio is methylthio or ethylthio. C₁-C₃-Alkylthio isadditionally, for example, n-propylthio or 1-methylethylthio(isopropylthio). C₁-C₄-Alkylthio is additionally, for example,butylthio, 1-methylpropylthio (sec-butylthio), 2-methylpropylthio(isobutylthio) or 1,1-dimethylethylthio (tert-butylthio).C₁-C₆-Alkylthio is additionally, for example, pentylthio,1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio,1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio,3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio,1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio,2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio,2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio.C₁-C₈-Alkylthio is additionally, for example, heptylthio, octylthio,2-ethylhexylthio and positional isomers thereof. C₁-C₁₀-Alkylthio isadditionally, for example, nonylthio, decylthio and positional isomersthereof.

The term “C₁-C₂-haloalkylthio” is a C₁-C₂-haloalkyl group, as definedabove, attached via a sulfur atom. The term “C₁-C₃-haloalkylthio” is aC₁-C₃-haloalkyl group, as defined above, attached via a sulfur atom. Theterm “C₁-C₄-haloalkylthio” is a C₁-C₄-haloalkyl group, as defined above,attached via a sulfur atom. The term “C₁-C₆-haloalkylthio” is aC₁-C₆-haloalkyl group, as defined above, attached via a sulfur atom. Theterm “C₁-C₁₀-haloalkylthio” is a C₁-C₁₀-haloalkyl group, as definedabove, attached via a sulfur atom. C₁-C₂-Haloalkylthio is, for example,SCH₂F, SCHF₂, SCF₃, SCH₂Cl, SCHC₂, SCCl₃, chlorofluoromethylthio,dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio,2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio,2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio or SC₂F₅.C₁-C₃-Haloalkylthio is additionally, for example, 2-fluoropropylthio,3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio,2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio,2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio,3,3,3-trichloropropylthio, SCH₂—C₂F₅, SCF₂—C₂F₅,1-(CH₂F)-2-fluoroethylthio, 1-(CH₂Cl)-2-chloroethylthio or1-(CH₂Br)-2-bromoethylthio. C₁-C₄-Haloalkylthio is additionally, forexample, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio ornonafluorobutylthio. C₁-C₆-Haloalkylthio is additionally, for example,5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio,5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio,6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio ordodecafluorohexylthio.

The term “C₁-C₂-alkylsulfinyl” is a C₁-C₂-alkyl group, as defined above,attached via a sulfinyl [S(O)] group. The term “C₁-C₄-alkylsulfinyl” isa C₁-C₄-alkyl group, as defined above, attached via a sulfinyl [S(O)]group. The term “C₁-C₆-alkylsulfinyl” is a C₁-C₆-alkyl group, as definedabove, attached via a sulfinyl [S(O)] group. The term“C₁-C₁₀-alkylsulfinyl” is a C₁-C₁₀-alkyl group, as defined above,attached via a sulfinyl [S(O)] group. C₁-C₂-Alkylsulfinyl ismethylsulfinyl or ethylsulfinyl. C₁-C₄-Alkylsulfinyl is additionally,for example, n-propylsulfinyl, 1-methylethylsulfinyl(isopropylsulfinyl), butylsulfinyl, 1-methylpropylsulfinyl(sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl) or1,1-dimethylethylsulfinyl (tert-butylsulfinyl). C₁-C₆-Alkylsulfinyl isadditionally, for example, pentylsulfinyl, 1-methylbutylsulfinyl,2-methylbutylsulfinyl, 3-methylbutylsulfinyl,1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl,2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl,1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl,4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl,1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl,2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl,3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl.C₁-C₈-Alkylsulfinyl is additionally, for example, heptylsulfinyl,octylsulfinyl, 2-ethylhexylsulfinyl and positional isomers thereof.C₁-C₁₀-Alkylsulfinyl is additionally, for example, nonylsulfinyl,decylsulfinyl and positional isomers thereof.

The term “C₁-C₂-haloalkylsulfinyl” is a C₁-C₂-haloalkyl group, asdefined above, attached via a sulfinyl [S(O)] group. The term“C₁-C₄-haloalkylsulfinyl” is a C₁-C₄-haloalkyl group, as defined above,attached via a sulfinyl [S(O)] group. The term “C₁-C₆-haloalkylsulfinyl”is a C₁-C₆-haloalkyl group, as defined above, attached via a sulfinyl[S(O)] group. The term “C₁-C₁₀-haloalkylsulfinyl” is a C₁-C₁₀-haloalkylgroup, as defined above, attached via a sulfinyl [S(O)] group.C₁-C₂-Haloalkylsulfinyl is, for example, S(O)CH₂F, S(O)CHF₂, S(O)CF₃,S(O)CH₂Cl, S(O)CHCl₂, S(O)CCl₃, chlorofluoromethylsulfinyl,dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl,2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl,2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl,2,2,2-trifluoroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl,2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl,2,2,2-trichloroethylsulfinyl or S(O)C₂F₅. C₁-C₄-Haloalkylsulfinyl isadditionally, for example, 2-fluoropropylsulfinyl,3-fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl,2,3-difluoropropylsulfinyl, 2-chloropropylsulfinyl,3-chloropropylsulfinyl, 2,3-dichloropropylsulfinyl,2-bromopropylsulfinyl, 3-bromopropylsulfinyl,3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl,S(O)CH₂—C₂F₅, S(O)CF₂—C₂F₅, 1-(CH₂F)-2-fluoroethylsulfinyl,1-(CH₂Cl)-2-chloroethylsulfinyl, 1-(CH₂Br)-2-bromoethylsulfinyl,4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl ornonafluorobutylsulfinyl. C₁-C₆-Haloalkylsulfinyl is additionally, forexample, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl,5-brompentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl,6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl,6-iodohexylsulfinyl or dodecafluorohexylsulfinyl.

The term “C₁-C₂-alkylsulfonyl” is a C₁-C₂-alkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term “C₁-C₃-alkylsulfonyl” isa C₁-C₃-alkyl group, as defined above, attached via a sulfonyl [S(O)₂]group. The term “C₁-C₄-alkylsulfonyl” is a C₁-C₄-alkyl group, as definedabove, attached via a sulfonyl [S(O)₂] group. The term“C₁-C₆-alkylsulfonyl” is a C₁-C₆-alkyl group, as defined above, attachedvia a sulfonyl [S(O)₂] group. The term “C₁-C₁₀-alkylsulfonyl” is aC₁-C₁₀-alkyl group, as defined above, attached via a sulfonyl [S(O)₂]group. C₁-C₂-Alkylsulfonyl is methylsulfonyl or ethylsulfonyl.C₁-C₃-Alkylsulfonyl is additionally, for example, n-propylsulfonyl or1-methylethylsulfonyl (isopropylsulfonyl). C₁-C₄-Alkylsulfonyl isadditionally, for example, butylsulfonyl, 1-methylpropylsulfonyl(sec-butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl) or1,1-dimethylethylsulfonyl (tert-butylsulfonyl). C₁-C₆-Alkylsulfonyl isadditionally, for example, pentylsulfonyl, 1-methylbutylsulfonyl,2-methylbutylsulfonyl, 3-methylbutylsulfonyl,1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl,2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl,1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl,4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl.C₁-C₈-Alkylsulfonyl is additionally, for example, heptylsulfonyl,octylsulfonyl, 2-ethylhexylsulfonyl and positional isomers thereof.C₁-C₁₀-Alkylsulfonyl is additionally, for example, nonylsulfonyl,decylsulfonyl and positional isomers thereof.

The term “C₁-C₂-haloalkylsulfonyl” is a C₁-C₂-haloalkyl group, asdefined above, attached via a sulfonyl [S(O)₂] group. The term“C₁-C₃-haloalkylsulfonyl” is a C₁-C₃-haloalkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term“C₁-C₄-haloalkylsulfonyl” is a C₁-C₄-haloalkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term“C₁-C₆-haloalkylsulfonyl” is a C₁-C₆-haloalkyl group, as defined above,attached via a sulfonyl [S(O)₂] group. The term“C₁-C₁₀-haloalkylsulfonyl” is a C₁-C₁₀-haloalkyl group, as definedabove, attached via a sulfonyl [S(O)₂] group. C₁-C₂-Haloalkylsulfonylis, for example, S(O)₂CH₂F, S(O)₂CHF₂, S(O)₂CF₃, S(O)₂CH₂Cl, S(O)₂CHCl₂,S(O)₂CCO₃, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl,chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl,2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl,2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl,2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl,2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl orS(O)₂CF₅. C₁-C₃-Haloalkylsulfonyl is additionally, for example,2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl,2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,2-chloropropylsulfonyl, 3-chloropropylsulfonyl,2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl,3-bromopropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,3,3,3-trichloropropylsulfonyl, S(O)₂CH₂—C₂F₅, S(O)₂CF₂—C₂F₅,1-(CH₂F)-2-fluoroethylsulfonyl, 1-(CH₂Cl)-2-chloroethylsulfonyl or1-(CH₂Br)-2-bromoethylsulfonyl. C₁-C₄-Haloalkylsulfonyl is additionally,for example, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl,4-bromobutylsulfonyl or nonafluorobutylsulfonyl. C₁-C₆-Haloalkylsulfonylis additionally, for example, 5-fluoropentylsulfonyl,5-chloropentylsulfonyl, 5-brompentylsulfonyl, 5-iodopentylsulfonyl,undecafluoropentylsulfonyl, 6-fluorohexylsulfonyl,6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl ordodecafluorohexylsulfonyl.

The substituent “oxo” replaces a CH₂ group by a C(═O) group.

The term “alkylcarbonyl” is a C₁-C₆-alkyl (“C₁-C₆-alkylcarbonyl”),preferably a C₁-C₄-alkyl (“C₁-C₄-alkylcarbonyl”) group, as definedabove, attached via a carbonyl [C(═O)] group. Examples are acetyl(methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl,isopropylcarbonyl, n-butylcarbonyl and the like.

The term “haloalkylcarbonyl” is a C₁-C₆-haloalkyl(“C₁-C₆-haloalkylcarbonyl”), preferably a C₁-C₄-haloalkyl(“C₁-C₄-haloalkylcarbonyl”) group, as defined above, attached via acarbonyl [C(═O)] group. Examples are trifluoromethylcarbonyl,2,2,2-trifluoroethylcarbonyl and the like.

The term “alkoxycarbonyl” is a C₁-C₆-alkoxy (“C₁-C₆-alkoxycarbonyl”),preferably a C₁-C₄-alkoxy (“C₁-C₄-alkoxycarbonyl”) group, as definedabove, attached via a carbonyl [C(═O)] group. Examples aremethoxycarbonyl), ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl,n-butoxycarbonyl and the like.

The term “haloalkoxycarbonyl” is a C₁-C₆-haloalkoxy(“C₁-C₆-haloalkoxycarbonyl”), preferably a C₁-C₄-haloalkoxy(“C₁-C₄-haloalkoxycarbonyl”) group, as defined above, attached via acarbonyl [C(═O)] group. Examples are trifluoromethoxycarbonyl,2,2,2-trifluoroethoxycarbonyl and the like.

The term “C₁-C₆-alkylamino” is a group —N(H)C₁-C₆-alkyl. Examples aremethylamino, ethylamino, propylamino, isopropylamino, butylamino and thelike.

The term “di-(C₁-C₆-alkyl)amino” is a group —N(C₁-C₆-alkyl)₂. Examplesare dimethylamino, diethylamino, ethylmethylamino, dipropylamino,diisopropylamino, methylpropylamino, methylisopropylamino,ethylpropylamino, ethylisopropylamino, dibutylamino and the like.

The term “3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partiallyunsaturated or maximally unsaturated heterocyclic ring containing 1, 2or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO,SO and SO₂, as ring members” denotes a 3-, 4-, 5-, 6- or 7-memberedsaturated, partially unsaturated or maximum unsaturated heteromonocyclicring or a 8-, 9- or 10-membered saturated, partially unsaturated ormaximally unsaturated heterobicyclic ring containing 1, 2 or 3 (or 4)heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂,as ring members.

Unsaturated rings contain at least one C—C and/or C—N and/or N—N doublebond(s). Maximally unsaturated rings contain as many conjugated C—Cand/or C—N and/or N—N double bonds as allowed by the ring size.Maximally unsaturated 5- or 6-membered heterocyclic rings are aromatic.The heterocyclic ring may be attached to the remainder of the moleculevia a carbon ring member or via a nitrogen ring member. As a matter ofcourse, the heterocyclic ring contains at least one carbon ring atom. Ifthe ring contains more than one O ring atom, these are not adjacent.

The term “3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturatedor maximum unsaturated heterocyclic ring containing 1, 2 or 3 (or 4)heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂,as ring members” [wherein “maximum unsaturated” includes also“aromatic”] as used herein denotes monocyclic radicals, the monocyclicradicals being saturated, partially unsaturated or maximum unsaturated(including aromatic). The term “3-, 4-, 5-, 6-, 7- or 8-memberedsaturated, partially unsaturated or maximum unsaturated heterocyclicring containing 1, 2 or 3 (or 4) heteroatoms or heteroatom groupsselected from N, O, S, NO, SO and SO₂, as ring members” [wherein“maximum unsaturated” includes also “aromatic”] as used herein furtheralso encompasses 8-membered heteromonocyclic radicals containing 1, 2 or3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SOand SO₂, as ring members, the monocyclic radicals being saturated,partially unsaturated or maximum unsaturated (including aromatic).Unsaturated rings contain at least one C—C and/or C—N and/or N—N doublebond(s). Maximum unsaturated rings contain as many conjugated C—C and/orC—N and/or N—N double bonds as allowed by the ring size. Maximumunsaturated 5- or 6-membered heterocyclic rings are aromatic. 7- and8-membered rings cannot be aromatic. They are homoaromatic (7-memberedring, 3 double bonds) or have 4 double bonds (8-membered ring). Theheterocyclic ring may be attached to the remainder of the molecule via acarbon ring member or via a nitrogen ring member. As a matter of course,the heterocyclic ring contains at least one carbon ring atom. If thering contains more than one O ring atom, these are not adjacent.

Examples of a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ringinclude: Oxiranyl, thiiranyl, aziridinyl, oxetanyl, thietanyl,azetidinyl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1-yl,pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1-yl, pyrazolidin-3-yl,pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1-yl,imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl,oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxazolidin-3-yl,isoxazolidin-4-yl, isoxazolidin-5-yl, thiazolidin-2-yl,thiazolidin-3-yl, thiazolidin-4-yl, thiazolidin-5-yl,isothiazolidin-2-yl, isothiazolidin-3-yl, isothiazolidin-4-yl,isothiazolidin-5-yl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-1-yl,1,3,4-triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl,1,3-dioxan-5-yl, 1,4-dioxan-2-yl, piperidin-1-yl, piperidin-2-yl,piperidin-3-yl, piperidin-4-yl, hexahydropyridazin-3-yl,hexahydropyridazin-4-yl, hexahydropyrimidin-2-yl,hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1-yl,piperazin-2-yl, 1,3,5-hexahydrotriazin-1-yl, 1,3,5-hexahydrotriazin-2-yland 1,2,4-hexahydrotriazin-3-yl, morpholin-2-yl, morpholin-3-yl,morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl,thiomorpholin-4-yl, 1-oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl,1-oxothiomorpholin-4-yl, 1,1-dioxothiomorpholin-2-yl,1,1-dioxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-4-yl, azepan-1-,-2-, -3- or -4-yl, oxepan-2-, -3-, -4- or -5-yl,hexahydro-1,3-diazepinyl, hexahydro-1,4-diazepinyl,hexahydro-1,3-oxazepinyl, hexahydro-1,4-oxazepinyl,hexahydro-1,3-dioxepinyl, hexahydro-1,4-dioxepinyl and the like.

Examples of a 3-, 4-, 5-, 6- or 7-membered partially unsaturatedheterocyclic ring include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl,2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl,2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl,2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl,2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl,2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl,2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl,2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl,2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl,2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl,2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl,3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl,4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl,2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- ortetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- ortetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- ortetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1,3,5-di- ortetrahydrotriazin-2-yl, 1,2,4-di- or tetrahydrotriazin-3-yl,2,3,4,5-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl,3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl,2,3,4,7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl,2,3,6,7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl,tetrahydrooxepinyl, such as 2,3,4,5-tetrahydro[1H]oxepin-2-, -3-, -4-,-5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6-or -7-yl, 2,3,6,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl,tetrahydro-1,3-diazepinyl, tetrahydro-1,4-diazepinyl,tetrahydro-1,3-oxazepinyl, tetrahydro-1,4-oxazepinyl,tetrahydro-1,3-dioxepinyl and tetrahydro-1,4-dioxepinyl.

Examples for a 3-, 4-, 5-, 6- or 7-membered maximally unsaturated(including aromatic) heterocyclic ring are 5- or 6-memberedheteroaromatic rings, such as 2-furyl, 3-furyl, 2-thienyl, 3-thienyl,1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl,4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl,2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl,4-imidazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 2-pyridinyl,3-pyridinyl, 4-pyridinyl, 1-oxopyridin-2-yl, 1-oxopyridin-3-yl,1-oxopyridin-4-yl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl,4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl, and also homoaromaticradicals, such as 1H-azepine, 1H-[1,3]-diazepine and 1H-[1,4]-diazepine.

Examples for a 8-, 9- or 10-membered saturated heterobicyclic ringcontaining 1, 2 or 3 (or 4) heteroatoms or heteroatom groups selectedfrom N, O, S, NO, SO and SO₂, as ring members are:

Examples for a 8-, 9- or 10-membered partially unsaturatedheterobicyclic ring containing 1, 2 or 3 (or 4) heteroatoms orheteroatom groups selected from N, O, S, NO, SO and SO₂, as ring membersare:

Examples for a 8-, 9- or 10-membered maximally unsaturatedheterobicyclic ring containing 1, 2 or 3 (or 4) heteroatoms orheteroatom groups selected from N, O, S, NO, SO and SO₂, as ring membersare:

In the above structures # denotes the attachment point to the remainderof the molecule. The attachment point is not restricted to the ring onwhich is shown, but can be on either of the fused rings, and may be on acarbon or on a nitrogen ring atom. If the rings carry one or moresubstituents, these may be bound to carbon and/or to nitrogen ring atoms(if the latter are not part of a double bond).

A saturated 3-, 4-, 5-, 6-, 7-, 8- or 9-membered ring, wherein the ringmay contain 1 or 2 heteroatoms or heteroatom groups selected from O, S,N, NR¹⁴, NO, SO and SO₂ and/or 1 or 2 groups selected from C═O, C═S andC═NR¹⁴ as ring members is either carbocyclic or heterocyclic. Examplesare, in addition to the saturated heteromonocyclic rings mentionedabove, carbocyclic rings, such as cyclopropyl, cyclopropanonyl,cyclobutyl, cyclobutanonyl, cyclopentyl, cyclopentanonyl, cyclohexyl,cyclohexanonyl, cyclohexadienonyl, cycloheptyl, cycloheptanonyl,cyclooctyl, cyclooctanonyl, furan-2-onyl, pyrrolidine-2-onyl,pyrrolidine-2,5-dionyl, piperidine-2-only, piperidine-2,6-dionyl and thelike.

The remarks made below concerning preferred embodiments of the variablesof the compounds of formula I, especially with respect to theirsubstituents A, A¹, A², A³, A⁴, B¹, B², B³, G¹, G², G³, G⁴, R¹, R²,R^(3a), R^(3b), R^(3c), R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R^(10a), R^(10b), R¹¹,R¹², R¹³, R¹⁴, R^(14a), R^(14b), R¹⁵, R¹⁶, m and n, the features of theuse and method according to the invention and of the composition of theinvention are valid both on their own and, in particular, in everypossible combination with each other.

In one embodiment of the invention, A is A¹.

In one preferred embodiment, A¹ is selected from —C(═NR⁶)R⁸ and —N(R⁵)R⁶and is more preferably —C(═NR⁶)R⁸; wherein R⁵, R⁶ and R⁸ have one of theabove general meanings, or, in particular, one of the below preferredmeanings.

R⁶ as a radical in the group —C(═NR⁶)R⁸ is preferably selected fromhydrogen, cyano, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl,C₂-C₁₀-alkynyl, wherein the four last-mentioned aliphatic andcycloaliphatic radicals each independently may be partially or fullyhalogenated and/or may be substituted with 1, 2, 3, 4, 5 or 6,preferably 1, 2 or 3, in particular 1, substituents R⁸; OR⁹ andNR^(10a)R^(10b); wherein R⁸, R⁹, R^(10a) and R^(10b) have one of theabove general meanings, or, in particular, one of the below preferredmeanings.

More preferably, R⁶ in —C(═NR⁶)R⁸ is selected from hydrogen,C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, wherein the two last-mentioned aliphaticand cycloaliphatic radicals each independently may be partially or fullyhalogenated and/or may be substituted with 1, 2 or 3, preferably 1 or 2,in particular 1, substituents R⁸; OR⁹ and NR^(10a)R^(10b); wherein R⁸,R⁹, R^(10a) and R^(10b) have one of the above general meanings, or, inparticular, one of the below preferred meanings.

Even more preferably, R⁶ in —C(═NR⁶)R⁸ is selected from OR⁹ andNR^(10a)R^(10b); wherein R⁸, R⁹, R^(10a) and R^(10b) have one of theabove general meanings, or, in particular, one of the below preferredmeanings.

In OR⁹ as a preferred meaning of R⁶ in —C(═NR⁶)R⁸, R⁹ is preferablyselected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl-, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl and C₂-C₆-haloalkynyl, and morepreferably from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl andC₃-C₈-cycloalkyl-C₁-C₄-alkyl-.

In NR^(10a)R^(10b) as a preferred meaning of R⁶ in —C(═NR⁶)R⁸, R^(10a)and R^(10b), independently of each other, are selected from the groupconsisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl,—C(═O)OR¹⁵, —C(═O)N(R^(14a))R^(14b), —C(═S)N(R^(14a))R^(14b), phenylwhich is optionally substituted with 1, 2, 3 or 4, substituents R¹⁶, anda 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated ormaximally unsaturated heterocyclic ring comprising 1, 2, 3 or 4heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂,as ring members, where the heterocyclic ring is optionally substitutedwith one or more substituents R¹⁶;

or R^(10a) and R^(10b) form together with the nitrogen atom they arebonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partiallyunsaturated or maximally unsaturated heterocyclic ring, wherein theheterocyclic ring may additionally contain one or two heteroatoms orheteroatom groups selected from N, O, S, NO, SO and SO₂, as ringmembers, where the heterocyclic ring optionally carries one or moresubstituents selected from halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl and C₂-C₆-haloalkynyl;wherein R^(14a), R^(14b) and R¹⁶ have one of the above general meanings,or, in particular, one of the below preferred meanings.

More preferably,

-   R^(10a) is selected from hydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl;    and-   R^(10b) is selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl, —C(═O)OR¹⁵,    —C(═O)N(R^(14a))R^(14b), —C(═S)N(R^(14a))R^(14b), phenyl which is    optionally substituted with 1, 2, 3 or 4, substituents R¹⁶, and a 5-    or 6-membered heteroaromatic ring comprising 1, 2 or 3 heteroatoms    selected from N, O and S, as ring members, where the heteroaromatic    ring is optionally substituted with one or more substituents R¹⁶;    -   wherein R^(14a), R^(14b) and R¹⁶ have one of the above general        meanings, or, in particular, one of the below preferred        meanings.

In the above radicals R^(10a) and R^(10b),

-   R^(14a) is selected from hydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl;    and-   R^(14b) is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,    C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,    C₃-C₆-cycloalkyl-C₁-C₄-alkyl-, C₁-C₆-alkyl substituted with a CN    group, C₁-C₆-alkoxyl, C₁-C₆-haloalkoxy, phenyl which is optionally    substituted with 1, 2, 3 or 4, substituents each independently    selected from the group consisting of halogen, cyano, nitro,    C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl,    C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,    C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; and a heterocyclic ring    selected from rings of formulae E-1 to E-51 defined below.

In an alternatively preferred embodiment, R^(11a) and R^(10b),independently of each other, are selected from the group consisting ofhydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl,—C(═O)N(R^(14a))R^(14b), —C(═S)N(R^(14a))R^(14b), phenyl which isoptionally substituted with 1, 2, 3 or 4, preferably 1, 2 or 3, inparticular 1, substituents R¹⁶, and a 3-, 4-, 5-, 6- or 7-memberedsaturated, partially unsaturated or maximally unsaturated heterocyclicring comprising 1, 2, 3 or 4 heteroatoms or heteroatom groups selectedfrom N, O, S, NO, SO and SO₂, as ring members, where the heterocyclicring is optionally substituted with one or more, preferably 1, 2 or 3,in particular 1, substituents R¹⁶;

-   or R^(10a) and R^(10b) form together with the nitrogen atom they are    bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially    unsaturated or maximally unsaturated heterocyclic ring, wherein the    heterocyclic ring may additionally contain one or two heteroatoms or    heteroatom groups selected from N, O, S, NO, SO and SO₂, as ring    members, where the heterocyclic ring optionally carries one or more,    preferably 1, 2 or 3, in particular 1, substituents selected from    halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,    C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,    C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,    C₂-C₆-haloalkenyl, C₂-C₆-alkynyl and C₂-C₆-haloalkynyl; wherein    R^(14a), R^(14b) and R¹⁶ have one of the above general meanings, or,    in particular, one of the below preferred meanings.

In an alternatively more preferred embodiment,

-   R^(10a) is selected from hydrogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl;    and-   R^(10b) is selected from —C(═O)N(R^(14a))R^(14b),    —C(═S)N(R^(14a))R^(14b), phenyl which is optionally substituted with    1, 2, 3 or 4, preferably 1, 2 or 3, in particular 1, substituents    R¹⁶, and a 5- or 6-membered heteroaromatic ring comprising 1, 2 or 3    heteroatoms selected from N, O and S, as ring members, where the    heteroaromatic ring is optionally substituted with one or more,    preferably 1, 2 or 3, in particular 1, substituents R¹⁶;    -   wherein R^(14a), R^(14b) and R¹⁶ have one of the above general        meanings, or, in particular, one of the below preferred        meanings.

In the above radicals R^(10a) and R^(10b) of the above alternativelypreferred and more preferred embodiments,

-   R^(14a) is preferably selected from hydrogen, C₁-C₆-alkyl and    C₁-C₆-haloalkyl; and-   R^(14b) is preferably selected from hydrogen, C₁-C₆-alkyl,    C₁-C₆-haloalkyl, C₁-C₆-alkenyl, C₁-C₆-haloalkenyl, C₃-C₆-cycloalkyl,    C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl-, C₁-C₆-alkyl    substituted with a CN group, phenyl which is optionally substituted    with 1, 2, 3 or 4, preferably 1, 2 or 3, in particular 1,    substituents R¹⁶, which are each independently preferably selected    from the group consisting of halogen, cyano, nitro, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,    C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,    C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and    C₂-C₄-haloalkynyl; and a heterocyclic ring selected from rings of    following formulae E-1 to E-51:

-   -   wherein    -   k is 0, 1, 2 or 3, n is 0, 1 or 2,    -   n is 0, 1 or 2; and    -   each R¹⁶ is independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,        C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and        C₂-C₄-haloalkynyl; or two R¹⁶ present on the same carbon atom of        a saturated ring may form together a group ═O or ═S.

More preferably, in the above radicals R^(10a) and R^(10b),

-   R^(14a) is selected from hydrogen and methyl; and-   R^(14b) is selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,    C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₃-C₆-cycloalkyl,    C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-methyl-, C₁-C₆-alkyl    substituted with a CN group, phenyl which is optionally substituted    with 1, 2, 3 or 4, preferably 1, 2 or 3, in particular 1,    substituents R¹⁶ selected from the group consisting of halogen,    cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,    C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl,    C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; and a    4-membered saturated heterocyclic ring comprising one heteroatom or    heteroatom group selected from S, SO and SO₂ as ring member (ring    E-44), where the heterocyclic ring is optionally substituted with    one or more, preferably 1 or 2, in particular 1, substituents R¹⁶;    -   wherein each R¹⁶ is independently selected from the group        consisting of halogen, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl,        C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,        C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; or    -   two R¹⁶ present on the same carbon atom may form together a        group ═O or ═S.

Preferably, in the above radicals, each R¹⁶ is independently selectedfrom halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy.

Specifically, in the above radicals R^(11a) and R^(10b),

-   R^(14a) is selected from hydrogen and methyl, and is specifically    hydrogen; and-   R^(14b) is selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and    C₃-C₆-cycloalkyl-methyl-.-   R⁸ as a radical in the group —C(═NR⁶)R⁸ is preferably selected from    hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and NR^(10a)R^(10b), and more    preferably from hydrogen and NR^(10a)R^(10b), and is specifically    hydrogen.

In this case (i.e. in NR^(10a)R^(10b) as a meaning of R⁸), R^(10a) andR^(10b) are preferably selected, independently of each other, fromhydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,C₁-C₄-alkylaminocarbonyl, C₁-C₄-haloalkylaminocarbonyl,C₃-C₆-cycloalkylaminocarbonyl and C₃-C₆-halocycloalkylaminocarbonyl,

-   or, together with the nitrogen atom to which they are bound, form a    5- or 6-membered saturated, partially unsaturated or aromatic    heterocyclic ring, which additionally may contain 1 or 2 further    heteroatoms or heteroatom groups selected from N, O, S, NO, SO and    SO₂, as ring members, where the heterocyclic ring may carry 1 or 2,    in particular 1, substituents selected from halogen, CN,    C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,    C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl,    C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₄-alkylthio and C₁-C₄-haloalkylthio.

More preferably, R^(10a) and R^(10b) are in this case selected,independently of each other, from hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,C₁-C₄-alkylaminocarbonyl and C₁-C₄-haloalkylaminocarbonyl.

In an alternative embodiment of the invention, A is A².

In A², W is preferably O.

In A², Y is preferably N(R⁵)R⁶; wherein R⁵ and R⁶ have one of the abovegeneral meanings, or, in particular, one of the below preferredmeanings.

In an alternatively preferred embodiment, in A²Y is hydrogen.

In an alternatively preferred embodiment, in A²Y is —OR⁹. R⁹ has one ofthe above general meanings, or, in particular, is selected fromhydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl and C₁-C₆-alkyl substituted byone radical R¹³, where R¹³ has one of the above general meanings, or, inparticular, one of the below preferred meanings.

More preferably, in A², W is O and Y is N(R⁵)R⁶; wherein R⁵ and R⁶ haveone of the above general meanings, or, in particular, one of the belowpreferred meanings.

In alternatively more preferred embodiment, in A², W is O and Y H.

In alternatively more preferred embodiment, in A², W is O and Y is —OR⁹,where R⁹ has one of the above general meanings, or, in particular, isselected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl and C₁-C₆-alkylsubstituted by one radical R¹³, where R¹³ has one of the above generalmeanings, or, in particular, one of the below preferred meanings.

In N(R⁵)R⁶ as a radical Y,

-   R⁵ is preferably selected from hydrogen, C₁-C₆-alkyl,    C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,    C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl and C₃-C₈-halocycloalkyl, where    the aforementioned aliphatic and cycloaliphatic radicals may be    substituted by 1, 2 or 3, preferably 1, radicals R⁸; and-   R⁶ is preferably selected from hydrogen, C₁-C₁₀-alkyl,    C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the four    last-mentioned aliphatic and cycloaliphatic radicals may be    partially or fully halogenated and/or may be substituted by one or    more, preferably 1, 2 or 3, in particular 1, substituents R⁸,    -   OR⁹, NR^(10a)R^(10b), S(O)_(n)R⁹,        C(═O)NR^(10a)N(R^(10a)R^(10b)), C(═O)R⁸,    -   phenyl which may be substituted with 1, 2, 3, 4, or 5,        preferably 1, 2 or 3, in particular 1, substituents R¹¹, and    -   a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially        unsaturated or maximally unsaturated heteromonocyclic or        heterobicyclic ring containing 1, 2, 3 or 4 heteroatoms or        heteroatom groups independently selected from N, O, S, NO, SO        and SO₂, as ring members, where the heteromonocyclic or        heterobicyclic ring may be substituted with one or more,        preferably 1, 2 or 3, in particular 1, substituents R¹¹;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated,        partially unsaturated or maximally unsaturated heterocyclic        ring, where the ring may further contain 1, 2, 3 or 4        heteroatoms or heteroatom-containing groups selected from O, S,        SO, SO₂, N, NH, C═O and C═S as ring members, wherein the        heterocyclic ring may be substituted with 1, 2, 3, 4 or 5,        preferably 1, 2 or 3, in particular 1, substituents        independently selected from the group consisting of halogen,        cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,        C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, wherein the        aliphatic or cycloaliphatic moieties in the twelve        last-mentioned radicals may be substituted by one or more,        preferably 1, 2 or 3, in particular 1, radicals R⁸, and phenyl        which may be substituted with 1, 2, 3, 4 or 5, preferably 1, 2        or 3, in particular 1, substituents R¹¹;    -   or    -   R⁵ and R⁶ together form a group ═C(R⁸)₂, ═S(O)_(m)(R⁹)₂,        ═NR^(10a) or ═NOR⁹;    -   wherein R⁸, R⁹, R^(10a), R^(10b) and R¹¹ have one of the above        general meanings, or, in particular, one of the below preferred        meanings.

More preferably, in N(R⁵)R⁶ as a radical Y,

-   R⁵ is selected from hydrogen, C₁-C₆-alkyl, C₂-C₃-alkynyl and    —CH₂—CN; and-   R⁶ is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₂-C₆-alkenyl, C₂-C₁₀-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,    C₃-C₆-halocycloalkyl, where the four last-mentioned aliphatic and    cycloaliphatic radicals may carry 1, 2 or 3 radicals R⁸;    C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, N(R^(10a))R^(10b), phenyl which may    be substituted with 1, 2, 3, 4, or 5 substituents R¹¹, and a 3-, 4-,    5-, 6- or 7-membered saturated, partially unsaturated or maximally    unsaturated heteromonocyclic ring containing 1, 2 or 3 heteroatoms    or heteroatom groups independently selected from N, O, S, NO, SO and    SO₂, as ring members, where the heteromonocyclic ring may be    substituted with one or more substituents R¹¹;    -   wherein R⁸ and R¹¹ are as defined in claim 1;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 3-, 4-, 5- or 6-membered saturated heterocyclic        ring, where the ring may further contain 1 or 2 heteroatoms or        heteroatom-containing groups selected from O, S, SO, SO₂, NH and        C═O as ring members, wherein the heterocyclic ring may be        substituted with 1, 2, 3, 4 or 5 substituents independently        selected from the group consisting of halogen, cyano,        C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a group ═S(R⁹)₂, where R⁹ is selected from        C₁-C₆-alkyl and C₁-C₆-haloalkyl.

Even more preferably, in N(R⁵)R⁶ as a radical Y,

-   R⁵ is selected from hydrogen, C₁-C₆-alkyl, C₂-C₃-alkynyl and CH₂—CN;    and-   R⁶ is selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkyl which    carries one radical R⁸, C₂-C₆-alkenyl, C₂-C₁₀-haloalkenyl,    C₂-C₆-alkynyl, C₃-C₆-cycloalkyl which may be substituted by 1 or 2    substituents selected from F, CN and pyridyl;    -   C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, N(R^(10a))R^(10b),    -   phenyl which may be substituted with 1, 2, 3, 4, or 5        substituents R¹¹, and a 3-, 4-, 5- or 6-membered saturated,        partially unsaturated or maximally unsaturated heteromonocyclic        ring containing 1, 2 or 3 heteroatoms or heteroatom groups        independently selected from N, O, S, NO, SO and SO₂, as ring        members, where the heteromonocyclic ring may be substituted with        one or more substituents R¹¹;    -   wherein R⁸ and R¹¹ are as defined in claim 1;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 3-, 4-, 5- or 6-membered saturated heterocyclic        ring, where the ring may further contain 1 or 2 heteroatoms or        heteroatom-containing groups selected from O, S, SO, SO₂, NH and        C═O as ring members, wherein the heterocyclic ring may be        substituted with 1, 2 or 3 substituents independently selected        from the group consisting of halogen, cyano, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a group ═S(R⁹)₂, where R⁹ is selected from        C₁-C₆-alkyl and C₁-C₆-haloalkyl.

Particularly preferably, in N(R⁵)R⁶ as a radical Y,

-   R⁵ selected from hydrogen, C₁-C₆-alkyl, C₂-C₃-alkynyl and CH₂—CN;    and-   R⁶ is selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkyl which    carries one radical R⁸, C₂-C₆-alkenyl, C₂-C₁₀-haloalkenyl,    C₂-C₆-alkynyl, C₃-C₆-cycloalkyl which may be substituted by 1 or 2    substituents selected from F, CN and pyridyl;    -   C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, N(R^(10a))R^(10b), wherein        RiG^(a) is selected from hydrogen and C₁-C₆-alkyl and R^(10b) is        selected from a 5- or 6-membered heteroaromatic ring containing        1, 2 or 3 heteroatoms selected from N, O and S as ring members,        where the heteroaromatic ring may be substituted with one or        more substituents R¹⁶;    -   phenyl which may be substituted with 1, 2, 3, 4, or 5        substituents R¹¹, and a 3-, 4-, 5- or 6-membered saturated,        partially unsaturated or maximally unsaturated heteromonocyclic        ring containing 1, 2 or 3 heteroatoms or heteroatom groups        independently selected from N, O, S, NO, SO and SO₂, as ring        members, where the heteromonocyclic ring may be substituted with        one or more substituents R¹¹;    -   wherein    -   each R¹¹ is independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,        C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and        C₂-C₄-haloalkynyl; or two R¹¹ present on the same carbon atom of        a saturated heterocyclic ring may form together ═O or ═S;    -   R⁸ is selected from OH, CN, C₃-C₈-cycloalkyl which optionally        carries a CN substituent, C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,        C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,        —C(═O)N(R^(10a))R^(10b), phenyl, optionally substituted with 1,        2, 3, 4 or 5 substituents R¹⁶, and a 3-, 4-, 5- or 6-membered        saturated, partially unsaturated or maximally unsaturated        heteromonocyclic ring containing 1, 2 or 3 heteroatoms or        heteroatom groups independently selected from N, O, S, NO, SO        and SO₂, as ring members, where the heteromonocyclic ring may be        substituted with one or more substituents R¹⁶;        -   wherein        -   R^(10a) is selected from the group consisting of hydrogen            and C₁-C₆-alkyl;        -   R^(10b) is selected from the group consisting of hydrogen,            C₁-C₆-alkyl, C₂-C₄-alkynyl, CH₂—CN, C₁-C₆-haloalkyl,            C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy and            C₁-C₄-haloalkoxy, and        -   each R¹⁶ as a substituent on phenyl or the heterocyclic            rings is independently selected from the group consisting of            halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,            C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,            C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and            C₂-C₄-haloalkynyl; or            -   two R¹⁶ present on the same carbon atom of a saturated                heterocyclic ring may form together ═O or ═S;-   or-   R⁵ and R⁶, together with the nitrogen atom to which they are bound,    form a 5- or 6-membered saturated heterocyclic ring, where the ring    may further contain 1 or 2 heteroatoms or heteroatom-containing    groups selected from O, S, SO, SO₂, NH and C═O as ring members,    wherein the heterocyclic ring may be substituted with 1, 2 or 3    substituents independently selected from the group consisting of    halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and    C₁-C₆-haloalkoxy;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a group ═S(R⁹)₂, where R⁹ is selected from        C₁-C₆-alkyl and C₁-C₆-haloalkyl.

Alternatively, more preferably, in N(R⁵)R⁶ as a radical Y,

-   R⁵ is selected from hydrogen, C₁-C₆-alkyl, C₂-C₃-alkynyl, CH₂—CN and    C₁-C₆-alkoxy-methyl-; and-   R⁶ is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, where the four    last-mentioned aliphatic and cycloaliphatic radicals may carry 1, 2    or 3, preferably 1, radicals R⁸; C(═O)R⁸, phenyl which may be    substituted with 1, 2, 3, 4, or 5 substituents R¹¹, and a 3-, 4-,    5-, 6- or 7-membered saturated, partially unsaturated or maximally    unsaturated heteromonocyclic ring containing 1, 2 or 3 heteroatoms    or heteroatom groups independently selected from N, O, S, NO, SO and    SO₂, as ring members, where the heteromonocyclic ring may be    substituted with one or more, preferably 1, 2 or 3, in particular 1,    substituents R¹¹;    -   wherein R⁸ and R¹¹ have one of the above general meanings, or,        in particular, one of the below preferred meanings;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 5- or 6-membered saturated heterocyclic ring,        where the ring may further contain 1 or 2 heteroatoms or        heteroatom-containing groups selected from O, S, SO, SO₂, NH and        C═O, preferably from O, NH and C═O, as ring members, wherein the        heterocyclic ring may be substituted with 1, 2, 3, 4 or 5        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and        C₁-C₆-haloalkoxy.

Preferably, the 3-, 4-, 5-, 6- or 7-membered saturated, partiallyunsaturated or maximally unsaturated heteromonocyclic ring R⁶ containing1, 2 or 3 heteroatoms or heteroatom groups independently selected fromN, O, S, NO, SO and SO₂, as ring members is selected from rings D-1 toD-173 listed below in context with A⁴. The ring may be substituted withone or more, preferably 1, 2 or 3, in particular 1, substituents R¹¹.

Alternatively, particularly preferably, in N(R⁵)R⁶ as a radical Y,

-   R⁵ is selected from hydrogen, C₁-C₆-alkyl, C₂-C₃-alkynyl, CH₂—CN and    C₁-C₆-alkoxy-methyl-; and-   R⁶ is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₃-C₆-cycloalkyl which may be substituted by 1 or 2 substituents    selected from F, CN, methyl and oxo;    -   C₁-C₄-alkyl which carries one radical R⁸; C(═O)R⁸, phenyl which        may be substituted with 1, 2, 3, 4, or 5 substituents R¹¹, and a        3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or        maximally unsaturated heteromonocyclic ring containing 1, 2 or 3        heteroatoms or heteroatom groups independently selected from N,        O, S, NO, SO and SO₂, as ring members, where the        heteromonocyclic ring may be substituted with one or more,        preferably 1, 2 or 3, in particular 1, substituents R¹¹;    -   wherein R⁸ and R¹¹ have one of the above general meanings, or,        in particular, one of the below preferred meanings;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 5- or 6-membered saturated heterocyclic ring,        where the ring may further contain 1 or 2 heteroatoms or        heteroatom-containing groups selected from O, S, SO, SO₂, NH and        C═O, preferably from O, NH and C═O, as ring members, wherein the        heterocyclic ring may be substituted with 1, 2 or 3 substituents        independently selected from the group consisting of halogen,        cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and        C₁-C₆-haloalkoxy.

Alternatively, even more preferably, in N(R⁵)R⁶ as a radical Y,

-   R⁵ is selected from hydrogen and C₁-C₆-alkyl; and-   R⁶ is selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkyl which    carries one radical R⁸, C₃-C₆-cycloalkyl which may be substituted by    1 or 2 substituents selected from F, CN, methyl and oxo,    -   C(═O)R⁸, phenyl which may be substituted with 1, 2, 3, 4, or 5        substituents R¹¹, and a 3-, 4-, 5- or 6-membered saturated,        partially unsaturated or maximally unsaturated heteromonocyclic        ring containing 1, 2 or 3 heteroatoms or heteroatom groups        independently selected from N, O, S, NO, SO and SO₂, as ring        members, where the heteromonocyclic ring may be substituted with        one or more substituents R¹¹;    -   wherein R⁸ and R¹¹ have one of the above general meanings, or,        in particular, one of the below preferred meanings;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 5- or 6-membered saturated heterocyclic ring,        where the ring may further contain 1 or 2 heteroatoms or        heteroatom-containing groups selected from O, S, SO, SO₂, NH and        C═O, preferably from O, NH and C═O, as ring members, wherein the        heterocyclic ring may be substituted with 1, 2 or 3 substituents        independently selected from the group consisting of halogen,        cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and        C₁-C₆-haloalkoxy.

Preferably the 3-, 4-, 5- or 6-membered saturated, partially unsaturatedor maximally unsaturated heteromonocyclic ring containing 1, 2 or 3heteroatoms or heteroatom groups independently selected from N, O, S,NO, SO and SO₂, as ring members is selected from rings D-1 to D-173listed below in context with A⁴, and more preferably from rings F-1 toF-51 listed below. The ring may be substituted with one or more,preferably 1, 2 or 3, in particular 1, substituents R¹.

In particular, in N(R⁵)R⁶ as a radical Y,

-   R⁵ is selected from hydrogen and methyl, preferably hydrogen; and-   R⁶ is selected from C₁-C₄-alkyl which carries one radical R⁸,    preferably methyl which carries one radical R⁸, C₁-C₄-haloalkyl, and    a 4-, 5- or 6-membered saturated heteromonocyclic ring containing 1    heteroatom or heteroatom group selected from S, SO and SO₂, as ring    member, where the heteromonocyclic ring may be substituted with one    or more substituents R¹¹;    -   wherein R⁸ and R¹¹ have one of the above general meanings, or,        in particular, one of the below preferred meanings;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 5- or 6-membered saturated heterocyclic ring (i.e.        R⁵ and R⁶ form together —(CH₂)₄— or —(CH₂)₅—), wherein the        heterocyclic ring may be substituted with 1, 2 or 3 substituents        independently selected from the group consisting of halogen,        cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and        C₁-C₆-haloalkoxy.

Preferably the 4-, 5- or 6-membered saturated heteromonocyclic ringcontaining 1 heteroatom or heteroatom group selected from S, SO and SO₂,as ring member is selected from rings D-72, D-77, D-78 and D-100 toD-102 listed below in context with A⁴. The ring may be substituted withone or more, preferably 1, 2 or 3, in particular 1, substituents R¹¹.More preference is given to ring D-72 with n=0 (thietan-3-yl) and itsoxidized analogs with n=1 and n=2 (1-oxo-thietan-3-yl and1,1-dioxo-thietan-3-yl)

In N(R⁵)R⁶ as a radical Y,

-   R⁸ as a substituent on an aliphatic or cycloaliphatic group is    preferably selected from cyano, C₃-C₈-cycloalkyl which may be    substituted by 1 or 2 substituents selected from CN, methyl and oxo,    C₃-C₈-halocycloalkyl, OR⁹, S(O)_(n)R⁹, N(R^(10a))R^(10b)    C(═O)N(R^(10a))R^(10b), C(═O)OR⁹, phenyl, optionally substituted    with 1, 2, 3, 4 or 5, preferably 1, 2 or 3, in particular 1,    substituents R¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated,    partially unsaturated or maximally unsaturated heterocyclic ring    comprising 1, 2 or 3 heteroatoms or heteroatom groups selected from    N, O, S, NO, SO and SO₂, as ring members, where the heterocyclic    ring is optionally substituted with one or more, preferably 1, 2 or    3, in particular 1, substituents R¹⁶; and-   R⁸ in the group C(═O)R⁸ is selected from hydrogen, C₁-C₆-alkyl,    C₁-C₆-haloalkyl, OR⁹ and N(R^(10a))R^(10b);    -   wherein R⁹, R^(10a), R^(10b) and R¹⁶ have one of the above        general meanings, or, in particular, one of the below preferred        meanings.

More preferably, in N(R⁵)R⁶ as a radical Y,

-   R⁸ as a substituent on an aliphatic or cycloaliphatic group is    selected from C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl,    —C(═O)N(R^(10a))R^(10b), —C(═S)N(R^(10a))R^(10b), —C(═O)OR⁹, phenyl,    optionally substituted with 1, 2, 3, 4 or 5, preferably 1, 2 or 3,    in particular 1, substituents R¹⁶, and a 3-, 4-, 5-, 6- or    7-membered saturated, partially unsaturated or maximally unsaturated    heterocyclic ring comprising 1, 2 or 3 heteroatoms or heteroatom    groups selected from N, O, S, NO, SO and SO₂, as ring members, where    the heterocyclic ring is optionally substituted with one or more,    preferably 1, 2 or 3, in particular 1, substituents R¹⁶;    -   or    -   two R⁸ present on the same carbon atom together form a group ═O,        ═C(R¹³)₂; ═S; ═S(O)_(m)(R¹⁵)₂, ═S(O)_(m)R¹⁵N(R^(14a))R^(14b),        ═NR^(10a), ═NOR⁹; or ═NNR^(10a)R^(10b);    -   and-   R⁸ in the group C(═O)R⁸ is selected from hydrogen, C₁-C₆-alkyl,    C₁-C₆-haloalkyl, OR⁹ and N(R^(10a))R^(10b);    -   wherein R⁹, R^(10a), R^(10b) and R¹⁶ have one of the above        general meanings, or, in particular, one of the below preferred        meanings.

Even more preferably, in N(R⁵)R⁶ as a radical Y, R⁸ as a substituent onan aliphatic or cycloaliphatic group is selected from—C(═O)N(R^(10a))R^(10b), phenyl and a 5- or 6-membered heteroaromaticring comprising 1, 2 or 3 heteroatoms selected from N, O and S, as ringmembers, where the heteroaromatic ring is optionally substituted withone or more, preferably 1, 2 or 3, in particular 1, substituents R¹⁶.

In this case,

-   R^(11a) and R^(10b) are preferably selected, independently of each    other, from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,    C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,    C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkylcarbonyl,    C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkylaminocarbonyl,    C₁-C₄-haloalkylaminocarbonyl, C₃-C₆-cycloalkylaminocarbonyl and    C₃-C₆-halocycloalkylaminocarbonyl, or, together with the nitrogen    atom to which they are bound, form a 5- or 6-membered saturated,    partially unsaturated or aromatic heterocyclic ring, which    additionally may contain 1 or 2 further heteroatoms or heteroatom    groups selected from N, O, S, NO, SO and SO₂, as ring members, where    the heterocyclic ring may carry 1 or 2, in particular 1,    substituents selected from halogen, CN, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,    C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,    C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio and    C₁-C₄-haloalkylthio.

More preferably, R^(10a) and R^(10b) are in this case selected,independently of each other, from hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,C₁-C₄-alkylaminocarbonyl and C₁-C₄-haloalkylaminocarbonyl. Specifically,they are selected, independently of each other, from hydrogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₃-C₆-cycloalkyl. Very specifically,one of R^(10a) and R^(10b) is hydrogen and the other is C₁-C₄-alkyl,C₁-C₄-haloalkyl or C₃-C₆-cycloalkyl.

In an alternative particular embodiment, in N(R⁵)R⁶ as Y,

-   R⁵ is hydrogen;-   R⁶ is selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alkyl which    carries one radical R⁸, C₃-C₆-cycloalkyl,    -   phenyl which may be substituted with 1, 2, 3, 4, or 5        substituents R¹¹, and a 4-, 5- or 6-membered saturated        heteromonocyclic ring containing 1 heteroatom or heteroatom        group selected from N, O, S, SO and SO₂, as ring member or a 5-        or 6-membered heteromonocyclic aromatic ring containing 1, 2 or        3 heteroatoms selected from O, N and S as ring members, where        the heteromonocyclic ring may be substituted with one or more        substituents R¹¹, where the heteromonocyclic ring is preferably        selected from rings of formulae F-1 to F-51:

-   -   wherein    -   k is 0, 1, 2 or 3,    -   n is 0, 1 or 2, and    -   each R¹¹ is independently selected from the group consisting of        halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,        C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and        C₂-C₄-haloalkynyl; or two R¹¹ present on the same carbon atom of        a saturated ring may form together ═O or ═S;    -   R⁸ is selected from C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl,        C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, —C(═O)N(R^(10a))R^(10b),        phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents        R¹⁶, and a heterocyclic ring selected from rings of formulae E-1        to E-51 as defined above;        -   wherein        -   R^(10a) is selected from the group consisting of hydrogen,            C₁-C₆-alkyl, C₂-C₃-alkynyl, —CH₂—CN and C₁-C₆-alkoxy-methyl;        -   R^(11b) is selected from the group consisting of hydrogen,            C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl,            C₃-C₆-cyclohaloalkyl, phenyl which is optionally substituted            with 1, 2, 3, 4 or 5 substituents selected from the group            consisting of halogen, cyano, nitro, C₁-C₄-alkyl,            C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,            C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl,            C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,            C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; and a heterocyclic ring            selected from rings of formulae E-1 to E-51 as defined            above; and        -   each R¹⁶ as a substituent on phenyl or a heterocyclic ring            E-1 to E-51 is independently selected from the group            consisting of halogen, cyano, nitro, C₁-C₄-alkyl,            C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,            C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl,            C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,            C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; or            -   two R¹⁶ present on the same carbon atom of a saturated                heterocyclic ring may form together ═O or ═S;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 5- or 6-membered saturated heterocyclic ring,        where the ring may further contain 1 or 2 heteroatoms or        heteroatom-containing groups selected from O, S, SO, SO₂, NH and        C═O as ring members, wherein the heterocyclic ring may be        substituted with 1, 2 or 3 substituents independently selected        from the group consisting of halogen, cyano, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy, and        preferably form a 5- or 6-membered saturated heterocyclic ring,        wherein the heterocyclic ring may be substituted with 1, 2 or 3        substituents independently selected from the group consisting of        halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy and        C₁-C₆-haloalkoxy.

Among the above rings, preference is given to F-44, F-48 and F-49.Particular preference is given to ring F-44 with n=0 (thietan-3-yl) andits oxidized analogs with n=1 and n=2 (1-oxo-thietan-3-yl and1,1-dioxo-thietan-3-yl).

Specifically, in A², W is O and Y is N(R⁵)R⁶, wherein

-   R⁵ is selected from hydrogen and methyl, preferably hydrogen; and-   R⁶ is selected from C₁-C₄-alkyl which carries one radical R⁸,    preferably methyl which carries one radical R⁸; C₁-C₄-haloalkyl, and    a 4-, 5- or 6-membered saturated heteromonocyclic ring containing 1    heteroatom or heteroatom group selected from S, SO and SO₂, as ring    member, where the heteromonocyclic ring may be substituted with one    or more substituents R¹¹;    -   wherein    -   R⁸ is selected from —C(═O)N(R^(10a))R^(10b), phenyl and a 5- or        6-membered heteroaromatic ring comprising 1, 2 or 3 heteroatoms        selected from N, O and S, as ring members, where the        heteroaromatic ring is optionally substituted with one or more,        preferably 1, 2 or 3, in particular 1, substituents R¹⁶,        -   wherein        -   R^(10a) and R^(10b) are selected, independently of each            other, from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,            C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,            C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,            C₁-C₄-alkylaminocarbonyl, C₁-C₄-haloalkylaminocarbonyl,            C₃-C₆-cycloalkylaminocarbonyl and            C₃-C₆-halocycloalkylaminocarbonyl, and preferably from            hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₃-C₆-cycloalkyl,            where it is preferred that one of R^(10a) and R^(10b) is            hydrogen and the other is C₁-C₄-alkyl, C₁-C₄-haloalkyl or            C₃-C₆-cycloalkyl;        -   each R¹¹ is independently selected from halogen, cyano,            nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,            C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,            C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl,            C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; and        -   each R¹⁶ is independently selected from halogen, cyano,            nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,            C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,            C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl,            C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and C₂-C₄-haloalkynyl;        -   or        -   R⁵ and R⁶, together with the nitrogen atom to which they are            bound, form a 5- or 6-membered saturated, partially            unsaturated or aromatic heterocyclic ring, which            additionally may contain 1 or 2 further heteroatoms or            heteroatom groups selected from N, O, S, NO, SO and SO₂, as            ring members, where the heterocyclic ring may carry 1 or 2,            in particular 1, substituents selected from halogen, CN,            C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,            C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,            C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy,            C₁-C₄-haloalkoxy, C₁-C₄-alkylthio and C₁-C₄-haloalkylthio,            and form preferably a 5- or 6-membered saturated            heterocyclic ring (i.e. R⁵ and R⁶ form together —(CH₂)₄— or            —(CH₂)₅—), wherein the heterocyclic ring may be substituted            with 1, 2 or 3 substituents independently selected from the            group consisting of halogen, cyano, C₁-C₆-alkyl,            C₁-C₆-haloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy.

Preferably the 4-, 5- or 6-membered saturated heteromonocyclic ring R⁶containing 1 heteroatom or heteroatom group selected from S, SO and SO₂,as ring member is selected from rings D-72 (═F-44), D-77 (═F-48), D-78(═F-49) and D-100 to D-102 listed below in context with A⁴. The ring maybe substituted with one or more, preferably 1, 2 or 3, in particular 1,substituents R¹¹ as defined above. More preference is given to ringsD-72 (═F-44), D-77 (═F-48) and D-78 (═F-49). Particular preference isgiven to ring D-72 (═F-44) with n=0 (thietan-3-yl) and its oxidizedanalogs with n=1 and n=2 (1-oxo-thietan-3-yl and1,1-dioxo-thietan-3-yl).

Preferably the 5- or 6-membered heteroaromatic ring comprising 1, 2 or 3heteroatoms selected from N, O and S, as ring members is selected fromrings E-1 to E-42 as defined above. The ring may be substituted with oneor more, preferably 1, 2 or 3, in particular 1, substituents R¹⁶selected from the group consisting of halogen, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyland C₂-C₄-haloalkynyl.

In an alternative embodiment of the invention, A is A³.

Preferably, R^(7a) and R^(7b) in the group A³ are independently of eachother selected from hydrogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl, and morepreferably one of R^(7a) and R^(7b) is hydrogen and the other ishydrogen or methyl. Specifically, both are hydrogen.

In the group A³,

-   R⁵ is preferably selected from hydrogen, C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the four    last-mentioned aliphatic and cycloaliphatic radicals may be    partially or fully halogenated and/or may be substituted with one or    more, preferably 1, 2 or 3, in particular 1, substituents R⁸; and-   R⁶ is preferably selected from hydrogen, C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the four    last-mentioned aliphatic and cycloaliphatic radicals may be    partially or fully halogenated and/or may be substituted by one or    more, preferably 1, 2 or 3, in particular 1, substituents R⁸,    -   —OR⁹, —NR^(10a)R^(10b), —S(O)_(n)R⁹,        —C(═O)NR^(10a)N(R^(10a)R^(10b)), —C(═O)R⁸, and a 3-, 4-, 5-, 6-        or 7-membered saturated, partially unsaturated or maximally        unsaturated heteromonocyclic or heterobicyclic ring containing        1, 2, 3 or 4 heteroatoms or heteroatom groups independently        selected from N, O, S, NO, SO and SO₂, as ring members, where        the heteromonocyclic or heterobicyclic ring may be substituted        with one or more, preferably 1, 2 or 3, in particular 1,        substituents R¹¹;    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 3-, 4-, 5- or 6-membered saturated, partially        unsaturated or maximally unsaturated heterocyclic ring, where        the ring may further contain 1, 2, 3 or 4 heteroatoms or        heteroatom-containing groups selected from O, S, N, SO, SO₂, C═O        and C═S as ring members, wherein the heterocyclic ring may be        substituted with 1, 2, 3, 4 or 5, preferably 1, 2 or 3, in        particular 1, substituents independently selected from the group        consisting of halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,        C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, wherein the aliphatic or cycloaliphatic        moieties in the twelve last-mentioned radicals may be        substituted by one or more, preferably 1, 2 or 3, in particular        1, radicals R⁸, and phenyl which may be substituted with 1, 2,        3, 4 or 5, preferably 1, 2 or 3, in particular 1, substituents        R¹¹;    -   or    -   R⁵ and R⁶ together form a group ═C(R⁸)₂, ═S(O)_(m)(R⁹)₂,        ═NR^(10a) or ═NOR⁹    -   wherein R⁸, R⁹, R^(10a), R^(10b) and R¹¹ have one of the above        general meanings, or, in particular, one of the below preferred        meanings.

More preferably, in the group A³,

-   R⁵ is selected from hydrogen, C₁-C₄-alkyl, which may be partially or    fully halogenated and/or may be substituted with one or more,    preferably 1, 2 or 3, in particular 1, substituents R⁸ selected from    cyano and C₁-C₆-alkoxy; and C₂-C₄-alkynyl; and-   R⁶ is selected from —S(O)_(n)R⁹ and —C(═O)R⁸,    -   or    -   R⁵ and R⁶, together with the nitrogen atom to which they are        bound, form a 3-, 4-, 5- or 6-membered saturated, partially        unsaturated or maximally unsaturated heterocyclic ring, where        the ring may further contain 1, 2, 3 or 4 heteroatoms or        heteroatom-containing groups selected from O, S, N, SO, SO₂, C═O        and C═S as ring members, wherein the heterocyclic ring may be        substituted with 1, 2, 3, 4 or 5, preferably 1, 2 or 3, in        particular 1, substituents independently selected from the group        consisting of halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,        C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl,        C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,        C₂-C₆-haloalkynyl, wherein the aliphatic or cycloaliphatic        moieties in the twelve last-mentioned radicals may be        substituted by one or more, preferably 1, 2 or 3, in particular        1, radicals R⁸, and phenyl which may be substituted with 1, 2,        3, 4 or 5, preferably 1, 2 or 3, in particular 1, substituents        R¹¹;    -   wherein R⁸, R⁹, R^(10a), R^(10b) and R¹¹ have one of the above        general meanings, or, in particular, one of the below preferred        meanings.

Even more preferably, in the group A³,

-   R⁵ is selected from hydrogen, C₁-C₄-alkyl, C₂-C₃-alkynyl, CH₂—CN and    C₁-C₆-alkoxy-methyl-, preferably from hydrogen and C₁-C₄-alkyl; and-   R⁶ is —C(═O)R⁸;    -   wherein R⁸ has one of the above general meanings, or, in        particular, one of the below preferred meanings.-   R⁸ in —C(═O)R⁸ as a meaning of the radicals R⁵ and R⁶ of the group    A³ is preferably selected from the group consisting of C₁-C₆-alkyl,    C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, where the    aliphatic and cycloaliphatic moieties in the four last-mentioned    radicals may be substituted by one or more, preferably 1, 2 or 3, in    particular 1, radicals R¹³;-   —OR⁹, —S(O)_(n)R⁹, —N(R^(10a))R^(10b),-   phenyl, optionally substituted with 1, 2, 3, 4 or 5, preferably 1, 2    or 3, in particular 1, substituents R¹⁶, and a 3-, 4-, 5- or    6-membered saturated, partially unsaturated or maximally unsaturated    heterocyclic ring comprising 1, 2 or 3 heteroatoms or heteroatom    groups selected from N, O, S, NO, SO and SO₂, as ring members, where    the heterocyclic ring is optionally substituted with one or more,    preferably 1, 2 or 3, in particular 1, substituents R¹⁶,-   wherein R⁹, R^(10a), R^(10b), R¹³ and R¹⁶ have one of the above    general meanings, or, in particular, one of the below preferred    meanings.

More preferably, R⁸ in —C(═O)R⁸ as a meaning of the radicals R⁵ and R⁶of the group A³ is selected from the group consisting of C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₄-alkyl substituted by one radical R¹³,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, —N(R^(10a))R^(10b), phenyl whichis optionally substituted with 1, 2, 3, 4 or 5 substituents eachindependently selected from the group consisting of halogen, cyano,nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyland C₂-C₄-haloalkynyl; and a heterocyclic ring selected from rings offormulae E-1 to E-51 as defined above.

R⁹ in —OR⁹ as a meaning of R⁸ in the group —C(═O)R⁸ as a meaning of theradicals R⁵ and R⁶ of the group A³ is preferably selected fromC₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyland C₃-C₈-cycloalkyl-C₁-C₄-alkyl-, and more preferably from C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl andC₃-C₈-cycloalkyl-C₁-C₄-alkyl-.

R^(10a) and R^(10b) in —N(R^(10a))R^(10b) as a meaning of R⁸ in thegroup —C(═O)R⁸ as a meaning of the radicals R⁵ and R⁶ of the group A³are, independently of each other, preferably selected from hydrogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkyl substituted by one radicalR¹³, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkylcarbonyl,C₁-C₄-haloalkylcarbonyl, C₁-C₄-alkylaminocarbonyl,C₁-C₄-haloalkylaminocarbonyl, C₃-C₆-cycloalkylaminocarbonyl,C₃-C₆-halocycloalkylaminocarbonyl, and a 3-, 4-, 5-, 6- or 7-memberedsaturated, partially unsaturated or maximally unsaturated heterocyclicring comprising 1, 2 or 3 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, as ring members, where the heterocyclic ring isoptionally substituted with one or more, preferably 1, 2 or 3, inparticular 1, substituents selected from halogen, CN, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio and C₁-C₄-haloalkylthio;

-   or, R^(10a) and R^(10b), together with the nitrogen atom to which    they are bound, form a 5- or 6-membered saturated, partially    unsaturated or aromatic heterocyclic ring, which additionally may    contain 1 or 2 further heteroatoms or heteroatom groups selected    from N, O, S, NO, SO and SO₂, as ring members, where the    heterocyclic ring may carry 1 or 2, in particular 1, substituents    selected from halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl,    C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,    C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkylthio and C₁-C₄-haloalkylthio.

More preferably, R^(10a) and R^(10b) in R⁸ in the radicals R⁵ and R⁶ ofthe group A³ are, independently of each other, selected from hydrogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkyl substituted by one radicalR¹³, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, and a 3- or 4-memberedsaturated heterocyclic ring comprising 1 heteroatom or heteroatom groupselected from N, O, S, NO, SO and SO₂, as ring member, where theheterocyclic ring is optionally substituted with one or more, preferably1, 2 or 3, in particular 1, substituents selected from halogen, CN,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; and arespecifically, independently of each other, selected from hydrogen,C₁-C₄-alkyl and C₁-C₄-haloalkyl.

R¹³ in R⁸ in the radicals R⁵ and R⁶ of the group A³ is preferablyselected from CN, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl,C₁-C₆-alkylsulfonyl and C₁-C₆-haloalkylsulfonyl.

R¹⁶ in R⁸ in the radicals R⁵ and R⁶ of the group A³ is preferablyselected from halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy.

Specifically, R⁸ in the group —C(═O)R⁸ in the radicals R⁵ and R⁶ of thegroup A³ is selected from the group consisting of C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₄-alkyl substituted by one radical R¹³,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, —N(R^(10a))R^(10b), phenyl whichis optionally substituted with 1, 2, 3, 4 or 5, preferably 1, 2 or 3 andin particular 1, substituents each independently selected from the groupconsisting of halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and C₂-C₄-haloalkynyl, and aheterocyclic ring selected from rings of formulae E-1 to E-51 as definedabove, wherein

-   R^(10a) and R^(10b), independently of each other, are selected from    hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₃-C₆-cycloalkyl;-   R¹³ is selected from CN, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,    C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkylsulfonyl and a heterocyclic ring selected from rings    of formulae E-1 to E-51 as defined above and preferably from    C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl and    C₁-C₆-haloalkylsulfonyl; and-   each R¹⁶ as a substituent on heterocyclic rings of formulae E-1 to    E-51 is independently selected from the group consisting of halogen,    cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,    C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl,    C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; or two R¹⁶    present on the same carbon atom of a saturated heterocyclic ring may    form together ═O or ═S.

More specifically, R⁸ in the group —C(═O)R⁸ in the radicals R⁵ and R⁶ ofthe group A³ is selected from the group consisting of C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₄-alkyl substituted by one radical R¹³,C₃-C₈-cycloalkyl and C₃-C₈-halocycloalkyl, where R¹³ is selected fromCN, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, preferably fromC₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl andC₁-C₆-haloalkylsulfonyl and in particular from C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfonyl and C₁-C₆-haloalkylsulfonyl.

Alternatively, in the group A³, R⁵ and R⁶ are in particular hydrogen.

In an alternative embodiment of the invention, A is A⁴.

A⁴ is preferably selected from a 3-, 4-, 5-, 6- or 7-membered saturated,partially unsaturated or maximally unsaturated heteromonocyclic ringcontaining 1, 2, 3 or 4 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, as ring members, where the heteromonocyclicring is optionally substituted with one or more, preferably 1, 2 or 3,in particular 1, substituents R¹¹, where R¹¹ has one of the abovegeneral meanings, or, in particular, one of the below preferredmeanings.

More preferably, A⁴ is selected from a 3-, 4-, 5-, 6- or 7-memberedsaturated heteromonocyclic ring containing 1 or 2 heteroatoms orheteroatom groups selected from N, O, S, NO, SO and SO₂, as ringmembers, a 5-, 6- or 7-membered partially unsaturated heteromonocyclicring containing 1, 2 or 3 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, as ring members, and a 5- or 6-memberedaromatic heteromonocyclic ring containing 1, 2, 3 or 4 heteroatomsselected from N, O and S as ring members, where the heteromonocyclicring is optionally substituted with one or more, preferably 1, 2 or 3,in particular 1, substituents R¹¹, where R¹¹ has one of the abovegeneral meanings, or, in particular, one of the below preferredmeanings.

A⁴ is even more preferably selected from rings of formulae D-1 to D-173

wherein k is 0, 1, 2 or 3, n is 0, 1 or 2 and R¹¹ has one of the abovegeneral meanings, or, in particular, one of the below preferredmeanings;and is in particular selected from D-59, D-65 and D-66 and isspecifically D-59.

Preferably, in the above rings D-1 to D-173,

-   each R¹¹ is independently selected from the group consisting of    halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,    C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl,    C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and C₂-C₄-haloalkynyl; or    -   two R¹¹ present on the same carbon atom of a saturated or        partially unsaturated ring may form together ═O or ═S.

Among the radicals A¹, A², A³ and A⁴, preference is given to A².

Preferably, B¹, B² and B³ are CR².

More preferably, B¹ and B³ are CR², where R² is not hydrogen, and B² isCR², where R² has one of the meanings given above.

Preferably, R² is selected from hydrogen, halogen, cyano, azido, nitro,—SCN, SF₅, C₁-C₆-alkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,wherein the four last mentioned aliphatic and cycloaliphatic radicalsmay be partially or fully halogenated and/or may be substituted by oneor more, preferably 1, 2 or 3, in particular 1, radicals R⁸, —OR⁹,—S(O)_(n)R⁹ and —NR^(10a)R^(10b),

wherein R⁸, R⁹, R^(10a) and R^(10b) have one of the above generalmeanings, or, in particular, one of the below preferred meanings.

More preferably, R² is selected from hydrogen, halogen andC₁-C₂-haloalkyl, even more preferably from hydrogen, F, Cl, Br and CF₃,even more preferably from hydrogen, F, C₁ and CF₃, and in particularfrom hydrogen and Cl.

Specifically, B² is CH and B¹ and B³ have one of the general or one ofthe preferred meanings given above for R² (with the proviso that theyare not hydrogen) and are preferably selected from halogen andC₁-C₂-haloalkyl, even more preferably from F, Cl, Br and CF₃,particularly preferably from hydrogen, F, C₁ and CF₃, and are inparticular Cl.

Alternatively, B² is CF or CCl and B¹ and B³ have one of the general orone of the preferred meanings given above for R² (with the proviso thatthey are not hydrogen) and are preferably selected from halogen andC₁-C₂-haloalkyl, such as F, C₁ and CF₃, even more preferably from F andCl, and are in particular Cl.

Preferably, G¹, G³ and G⁴ are CR⁴ and G² is N or CR⁴, where R⁴ has oneof the meanings given above or below; or G², G³ and G⁴ are CR⁴ and G¹ isN or CR⁴, where R⁴ has one of the meanings given above or below.

Preferably, R⁴ is selected from hydrogen, halogen, cyano, azido, nitro,C₁-C₆-alkyl which may be partially or fully halogenated and/or may besubstituted by one or more, preferably 1, 2 or 3, in particular 1,radicals R⁸, C₃-C₈-cycloalkyl which may be partially or fullyhalogenated and/or may be substituted by one or more, preferably 1, 2 or3, in particular 1, radicals R⁸, C₂-C₆-alkenyl which may be partially orfully halogenated and/or may be substituted by one or more, preferably1, 2 or 3, in particular 1, radicals R⁸, C₂-C₆-alkynyl which may bepartially or fully halogenated and/or may be substituted by one or more,preferably 1, 2 or 3, in particular 1, radicals R⁸, —OR⁹, —S(O)_(n)R⁹,and —NR^(10a)R^(10b). More preferably, R⁴ is selected from hydrogen,halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₅-cycloalkyl,C₃-C₅-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,C₂-C₄-haloalkynyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, and even more preferablyfrom hydrogen, halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₃-C₅-cycloalkyl, C₃-C₅-halocycloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio and C₁-C₄-haloalkylthio, andspecifically from hydrogen, methyl and CF₃.

More preferably, G¹, G³ and G⁴ are CH and G² is CR⁴, where R⁴ has one ofthe above general or preferred meanings; or G¹ is N, G³ and G⁴ are CHand G² is CR⁴.

In another embodiment, G¹ and G⁴ are CR⁴ and G² and G³ are CH, where R⁴has one of the meanings given above or below.

Even more preferably, G¹, G³ and G⁴ are CH and G² is CR⁴, where R⁴ isselected from hydrogen, halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio and C₁-C₄-haloalkylthio,preferably from hydrogen, F, Cl, CN, methyl, CF₃, methoxy andmethylthio, and specifically from hydrogen, F, Cl, CN, methyl methoxyand methylthio.

Alternatively, even more preferably, G¹ is N, G² is CR⁴ and G³ and G⁴are CH, where R⁴ is selected from hydrogen, halogen, cyano, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio andC₁-C₄-haloalkylthio, preferably from hydrogen, F, Cl, CN, methyl, CF₃,methoxy and methylthio, and specifically from hydrogen and methyl.

Preferably, R¹ is selected from C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkylC₃-C₆-halocycloalkyl or C(═O)OR¹³; more preferably, from C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl and C(═O)OR¹⁵,even more preferably from C₁-C₄-alkyl, C₁-C₄-haloalkyl and —C(═O)OR¹⁵,and particularly preferably from C₁-C₄-haloalkyl and —C(═O)OR¹⁵, whereinR¹⁵ is preferably C₁-C₄-alkyl. In particular, R¹ is C₁-C₄-haloalkyl,specifically C₁-C₂-haloalkyl and more specifically halomethyl, inparticular fluoromethyl, such as fluoromethyl, difluoromethyl andtrifluoromethyl, and is very specifically trifluoromethyl.

Preferably, R^(3a) and R^(3b) are selected, independently of each other,from hydrogen, halogen, hydroxyl, C₁-C₃-alkyl, C₁-C₃-alkenyl,C₁-C₃-alkynyl, C₁-C₃-haloalkyl, C₁-C₃-alkoxy, C₁-C₃-alkylthio andC₁-C₃-alkylsulfonyl, more preferably from hydrogen and halogen, inparticular from hydrogen and fluorine and are specifically hydrogen.

If not specified otherwise above, R⁸, R⁹, R^(10a), R^(10b), R¹¹, R¹²,R¹³, R¹⁴, R^(14a), R^(14b), R¹⁵ and R¹⁶ have following preferredmeanings:

In case R⁸ is a substituent on an alkyl, alkenyl or alkynyl group, it ispreferably selected from the group consisting of cyano,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, —OR⁹, —SR⁹,—C(═O)N(R^(10a))R^(10b), —C(═S)N(R^(10a))R^(10b), —C(═O)OR⁹, phenylwhich may be substituted by 1, 2, 3, 4 or 5 radicals R¹⁶, and a 3-, 4-,5-, 6- or 7-membered saturated, partially unsaturated or aromaticheterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groupsselected from N, O, S, NO, SO and SO₂, as ring members, where theheterocyclic ring may be substituted by one or more radicals R¹⁶; whereR⁹, R^(10a), R^(10b) and R¹⁶ have one of the meanings given above or inparticular one of the preferred meanings given below.

In case R⁸ is a substituent on an alkyl, alkenyl or alkynyl group, it iseven more preferably selected from the group consisting of cyano,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, —C(═O)N(R^(10a))R^(10b),—C(═S)N(R^(10a))R^(10b), —C(═O)OR⁹, phenyl which may be substituted by1, 2, 3, 4 or 5 radicals R¹⁶, and a 3-, 4-, 5-, 6- or 7-memberedsaturated, partially unsaturated or aromatic heterocyclic ringcontaining 1, 2 or 3 heteroatoms or heteroatom groups selected from N,O, S, NO, SO and SO₂, as ring members, where the heterocyclic ring maybe substituted by one or more radicals R¹⁶; where R⁹, R^(10a), R^(10b)and R¹⁶ have one of the meanings given above or in particular one of thepreferred meanings given below. In particular it is selected from thegroup consisting of cyano, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,—C(═O)N(R^(10a))R^(10b), —C(═S)N(R^(10a))R^(10b), —C(═O)OR⁹, phenylwhich may be substituted by 1, 2, 3, 4 or 5 radicals R¹⁶, and a 3-, 4-,5-, 6- or 7-membered saturated, partially unsaturated or aromaticheterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groupsselected from N, O, S, NO, SO and SO₂, as ring members, where theheterocyclic ring may be substituted by one or more radicals R¹⁶; whereR⁹, R^(10a), R^(10b) and R¹⁶ have one of the meanings given above or inparticular one of the preferred meanings given below.

In case R⁸ is a substituent on a cycloalkyl group, it is preferablyselected from the group consisting of cyano, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, —OR⁹, —OSO₂R⁹, —SR⁹,—N(R^(10a))R^(10b), —C(═O)N(R^(10a))R^(10b), —C(═S)N(R^(10a))R^(10b),—C(═O)OR⁹, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicalsR¹⁶, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturatedor aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms orheteroatom groups selected from N, O, S, NO, SO and SO₂, as ringmembers, where the heterocyclic ring may be substituted by one or moreradicals R¹⁶; where R⁹, R^(10a), R^(10b) and R¹⁶ have one of themeanings given above or in particular one of the preferred meaningsgiven below.

In case R⁸ is a substituent on a cycloalkyl group, it is even morepreferably selected from the group consisting of halogen, C₁-C₄-alkyl,C₁-C₃-haloalkyl, C₁-C₄-alkoxy and C₁-C₃-haloalkoxy. In particular, R⁸ asa substituent on a cycloalkyl group is selected from halogen,C₁-C₄-alkyl and C₁-C₃-haloalkyl.

In case of R⁸ in a group —C(═O)R⁸, ═C(R⁸)₂ or —C(═NR⁶)R⁸, R⁸ ispreferably selected from the group consisting of hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, —OR⁹, —SR⁹, —N(R^(10a))R^(10b), phenyl which may besubstituted by 1, 2, 3, 4 or 5 radicals R¹⁶, and a 3-, 4-, 5-, 6- or7-membered saturated, partially unsaturated or aromatic heterocyclicring containing 1, 2 or 3 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, as ring members, where the heterocyclic ringmay be substituted by one or more radicals R¹⁶; where R⁹, R^(10a),R^(10b) and R¹⁶ have one of the meanings given above or in particularone of the preferred meanings given below.

In case of R⁸ in a group —C(═O)R⁸, ═C(R⁸)₂ or —C(═NR⁶)R⁸, R⁸ is morepreferably selected from the group consisting of C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, —N(R^(10a))R^(10b), phenyl which may be substituted by1, 2, 3, 4 or 5 radicals R¹⁶, and a 3-, 4-, 5-, 6- or 7-memberedsaturated, partially unsaturated or aromatic heterocyclic ringcontaining 1, 2 or 3 heteroatoms or heteroatom groups selected from N,O, S, NO, SO and SO₂, as ring members, where the heterocyclic ring maybe substituted by one or more radicals R¹⁶; where RiG^(a), R^(10b) andR¹⁶ have has one of the meanings given above or in particular one of thepreferred meanings given below.

Preferably, each R⁹ is independently selected from the group consistingof hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, phenyl which may besubstituted by 1, 2, 3, 4 or 5 radicals R¹⁶; and a 3-, 4-, 5-, 6- or7-membered saturated, partially unsaturated or aromatic heterocyclicring containing 1, 2 or 3 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, as ring members, where the heterocyclic ringmay be substituted by one or more, e.g. 1, 2, 3 or 4, preferably 1 or 2,more preferably 1, radicals R¹⁶, where R¹⁶ has one of the meanings givenabove or in particular one of the preferred meanings given below.

More preferably, each R⁹ is independently selected from the groupconsisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, phenyl which maybe substituted by 1, 2, 3, 4 or 5 radicals R¹⁶; and a 5- or 6-memberedheteroaromatic ring containing 1, 2 or 3 heteroatoms selected from N, Oand S, as ring members, where the heteroaromatic ring may be substitutedby one or more radicals R¹⁶; where R¹⁶ has one of the meanings givenabove or in particular one of the preferred meanings given below.

R^(10a) and R^(10b) are, independently of each other, preferablyselected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₁-C₄-alkylcarbonyl, C₁-C₄-haloalkylcarbonyl,C₁-C₄-alkylaminocarbonyl, C₁-C₄-haloalkylaminocarbonyl,C₃-C₆-cycloalkylaminocarbonyl, C₃-C₆-halocycloalkylaminocarbonyl, and a3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated ormaximally unsaturated heterocyclic ring comprising 1, 2 or 3 heteroatomsor heteroatom groups selected from N, O, S, NO, SO and SO₂, as ringmembers, where the heterocyclic ring is optionally substituted with oneor more, preferably 1, 2 or 3, in particular 1, substituents selectedfrom halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthioand C₁-C₄-haloalkylthio;

or, R^(10a) and R^(10b), together with the nitrogen atom to which theyare bound, form a 5- or 6-membered saturated, partially unsaturated oraromatic heterocyclic ring, which additionally may contain 1 or 2further heteroatoms or heteroatom groups selected from N, O, S, NO, SOand SO₂, as ring members, where the heterocyclic ring may carry 1 or 2,in particular 1, substituents selected from halogen, CN, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio and C₁-C₄-haloalkylthio.

More preferably, R^(10a) and R^(10b) are, independently of each other,selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, and a 3- or 4-membered saturated heterocyclic ringcomprising 1 heteroatom or heteroatom group selected from N, O, S, NO,SO and SO₂, as ring member, where the heterocyclic ring is optionallysubstituted with one or more, preferably 1, 2 or 3, in particular 1,substituents selected from halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; and are specifically, independentlyof each other, selected from hydrogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl.

Each R¹¹ and each R¹⁶ are independently of each occurrence andindependently of each other preferably selected from halogen, CN,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulfinyl,C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl andC₁-C₄-haloalkylsulfonyl, and more preferably from halogen, CN,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

Each R¹² is preferably selected from C₁-C₄-alkyl and is in particularmethyl.

In case R¹³ is a substituent on an alkyl, alkenyl or alkynyl group, itis preferably selected from the group consisting of cyano,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, —OH, —SH, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,C₁-C₄-haloalkylsulfonyl and phenyl which may be substituted by 1, 2 or 3radicals selected from halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

In case R¹³ is a substituent on a cycloalkyl group, it is preferablyselected from the group consisting of cyano, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, —OH, —SH,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,C₁-C₄-alkylsulfinyl, C₁-C₄-haloalkylsulfinyl, C₁-C₄-alkylsulfonyl,C₁-C₄-haloalkylsulfonyl and phenyl which may be substituted by 1, 2 or 3radicals selected from halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

In case R¹³ is a substituent on a cycloalkyl group, it is even morepreferably selected from the group consisting of halogen, C₁-C₄-alkyl,C₁-C₃-haloalkyl, C₁-C₄-alkoxy and C₁-C₃-haloalkoxy. In particular, R¹³as a substituent on a cycloalkyl group is selected from halogen,C₁-C₄-alkyl and C₁-C₃-haloalkyl.

In case of R¹³ in a group —C(═O)R¹³, —C(═S)R¹³, ═C(R¹³)₂ or—C(═NR¹⁴)R¹³, R⁸ is preferably selected from the group consisting ofhydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, —OH, —SH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy andphenyl which may be substituted by 1, 2 or 3 radicals selected fromhalogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy.

R¹⁴, R^(14a) and R^(14b) are, independently of each other, preferablyselected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl and benzyl, where the phenyl ring in benzyl isoptionally substituted 1, 2 or 3, in particular 1, substituents selectedfrom halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy;

or, R^(14a) and R^(14b), together with the nitrogen atom to which theyare bound, form a 5- or 6-membered saturated, partially unsaturated oraromatic heterocyclic ring, which additionally may contain 1 or 2further heteroatoms or heteroatom groups selected from N, O, S, NO, SOand SO₂, as ring members, where the heterocyclic ring may carry 1 or 2,in particular 1, substituents selected from halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

More preferably, R¹⁴, R^(14a) and R^(14b) are, independently of eachother, selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl and benzyl, where the phenyl ringin benzyl is optionally substituted 1, 2 or 3, in particular 1,substituents selected from halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

or, R^(14a) and R^(14b), together with the nitrogen atom to which theyare bound, form a 5- or 6-membered saturated, partially unsaturated oraromatic heterocyclic ring, which additionally may contain 1 or 2further heteroatoms or heteroatom groups selected from N, O, S, NO, SOand SO₂, as ring members, where the heterocyclic ring may carry 1 or 2,in particular 1, substituents selected from halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

Each R¹⁵ is preferably selected from hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, phenyl, benzyl, pyridyl and phenoxy, wherein the fourlast-mentioned radicals may be unsubstituted and/or carry 1, 2 or 3substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxyand C₁-C₆-haloalkoxy.

In a particular embodiment of the invention, compound I is a compound offormula IA

where A, R² and R⁴ have one of the above-given general or, inparticular, one of the above-given preferred meanings, and R^(2a) andR^(2c), independently of each other, have one of the general or, inparticular, one of the preferred meanings given above for R², with theproviso that they are not hydrogen, and are specifically Cl or CF₃ andare very specifically Cl.

Examples of preferred compounds are compounds of the following formulaeIa.1 to Ia.31, where the variables have one of the general or preferredmeanings given above. Examples of preferred compounds are the individualcompounds compiled in the tables 1 to 2082 below, Moreover, the meaningsmentioned below for the individual variables in the tables are per se,independently of the combination in which they are mentioned, aparticularly preferred embodiment of the substituents in question.

Table 1

Compounds of the formula Ia.1 in which R^(14b) is hydrogen, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2

Compounds of the formula Ia.1 in which R^(14b) is methyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 3

Compounds of the formula Ia.1 in which R^(14b) is ethyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 4

Compounds of the formula Ia.1 in which R^(14b) is propyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 5

Compounds of the formula Ia.1 in which R^(14b) is isopropyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 6

Compounds of the formula Ia.1 in which R^(14b) is n-butyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 7

Compounds of the formula Ia.1 in which R^(14b) is sec-butyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 8

Compounds of the formula Ia.1 in which R^(14b) is isobutyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 9

Compounds of the formula Ia.1 in which R^(14b) is tert-butyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 10

Compounds of the formula Ia.1 in which R^(14b) is isopropenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 11

Compounds of the formula Ia.1 in which R^(14b) is cyclopropyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 12

Compounds of the formula Ia.1 in which R^(14b) is 2,2-difluoroethyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 13

Compounds of the formula Ia.1 in which R^(14b) is 2,2,2-trifluoroethyl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 14

Compounds of the formula Ia.1 in which R^(14b) is 3,3,3-trifluoropropyl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 15

Compounds of the formula Ia.1 in which R^(14b) is CH₂—CN, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 16

Compounds of the formula Ia.1 in which R^(14b) is CH₂-isopropenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 17

Compounds of the formula Ia.1 in which R^(14b) is CH₂-cyclopropyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 18

Compounds of the formula Ia.1 in which R^(14b) is thietan-3-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 19

Compounds of the formula Ia.1 in which R^(14b) is 1-oxo-thietan-3-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 20

Compounds of the formula Ia.1 in which R^(14b) is1,1-dioxo-thietan-3-yl, and the combination of R^(2a), R^(2b), R^(2c)and R⁴ for a compound corresponds in each case to one row of Table A

Table 21

Compounds of the formula Ia.1 in which R^(14b) is allyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 22

Compounds of the formula Ia.1 in which R^(14b) is propargyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 23

Compounds of the formula Ia.1 in which R^(14b) is methoxy, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 24

Compounds of the formula Ia.1 in which R^(14b) is ethoxy, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 25

Compounds of the formula Ia.1 in which R^(14b) is isopropoxy, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Tables 26 to 50

Compounds of the formula Ia.2 in which R^(14b) is as defined in any oftables 1 to 25 and the combination of R^(2a), R^(2b), R^(2c) and R⁴ fora compound corresponds in each case to one row of Table A

Tables 51 to 75

Compounds of the formula Ia.3 in which R^(14b) is as defined in any oftables 1 to 25 and the combination of R^(2a), R^(2b), R^(2c) and R⁴ fora compound corresponds in each case to one row of Table A

Tables 76 to 100

Compounds of the formula Ia.4 in which R^(14b) is as defined in any oftables 1 to 25 and the combination of R^(2a), R^(2b), R^(2c) and R⁴ fora compound corresponds in each case to one row of Table A

Tables 101 to 125

Compounds of the formula Ia.5 in which R^(14b) is as defined in any oftables 1 to 25 and the combination of R^(2a), R^(2b), R^(2c) and R⁴ fora compound corresponds in each case to one row of Table A

Tables 126 to 150

Compounds of the formula Ia.6 in which R^(14b) is as defined in any oftables 1 to 25 and the combination of R^(2a), R^(2b), R^(2c) and R⁴ fora compound corresponds in each case to one row of Table A

Tables 151 to 175

Compounds of the formula Ia.7 in which R^(14b) is as defined in any oftables 1 to 25 and the combination of R^(2a), R^(2b), R^(2c) and R⁴ fora compound corresponds in each case to one row of Table A

Tables 176 to 200

Compounds of the formula Ia.8 in which R^(14b) is as defined in any oftables 1 to 25 and the combination of R^(2a), R^(2b), R^(2c) and R⁴ fora compound corresponds in each case to one row of Table A

Table 201

Compounds of the formula Ia.9 in which R^(10b) is phenyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 202

Compounds of the formula Ia.9 in which R^(10b) is 2-fluorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 203

Compounds of the formula Ia.9 in which R^(10b) is 3-fluorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 204

Compounds of the formula Ia.9 in which R^(10b) is 4-fluorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 205

Compounds of the formula Ia.9 in which R^(10b) is 2-chlorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 206

Compounds of the formula Ia.9 in which R^(10b) is 3-chlorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 207

Compounds of the formula Ia.9 in which R^(10b) is 4-chlorophenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 208

Compounds of the formula Ia.9 in which R^(10b) is 2,3-difluorophenyl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 209

Compounds of the formula Ia.9 in which R^(10b) is 2,4-difluorophenyl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 210

Compounds of the formula Ia.9 in which R^(10b) is 2,5-difluorophenyl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 211

Compounds of the formula Ia.9 in which R^(10b) is 2,6-difluorophenyl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 212

Compounds of the formula Ia.9 in which R^(10b) is 3,4-difluorophenyl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 213

Compounds of the formula Ia.9 in which R^(10b) is 3,5-difluorophenyl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 214

Compounds of the formula Ia.9 in which R^(10b) is 3,4,5-trifluorophenyl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 215

Compounds of the formula Ia.9 in which R^(10b) is 2,4-dichlorophenyl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 216

Compounds of the formula Ia.9 in which R^(10b) is 3,5-dichlorophenyl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 217

Compounds of the formula Ia.9 in which R^(10b) is 2-methylphenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 218

Compounds of the formula Ia.9 in which R^(10b) is 3-methylphenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 219

Compounds of the formula Ia.9 in which R^(10b) is 4-methylphenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 220

Compounds of the formula Ia.9 in which R^(10b) is 2-methoxyphenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 221

Compounds of the formula Ia.9 in which R^(10b) is 3-methoxyphenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 222

Compounds of the formula Ia.9 in which R^(10b) is 4-methoxyphenyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 223

Compounds of the formula Ia.9 in which R^(10b) is pyridin-2-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 224

Compounds of the formula Ia.9 in which R^(10b) is 3-chloropyridin-2-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 225

Compounds of the formula Ia.9 in which R^(10b) is 4-chloropyridin-2-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 226

Compounds of the formula Ia.9 in which R^(10b) is 5-chloropyridin-2-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 227

Compounds of the formula Ia.9 in which R^(10b) is 6-chloropyridin-2-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 228

Compounds of the formula Ia.9 in which R^(10b) is 3-methoxypyridin-2-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 229

Compounds of the formula Ia.9 in which R^(10b) is 4-methoxypyridin-2-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 230

Compounds of the formula Ia.9 in which R^(10b) is 5-methoxypyridin-2-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 231

Compounds of the formula Ia.9 in which R^(10b) is 6-methoxypyridin-2-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 232

Compounds of the formula Ia.9 in which R^(10b) is pyridin-3-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 233

Compounds of the formula Ia.9 in which R^(10b) is 2-chloropyridin-3-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 234

Compounds of the formula Ia.9 in which R^(10b) is 4-chloropyridin-3-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 235

Compounds of the formula Ia.9 in which R^(10b) is 5-chloropyridin-3-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 236

Compounds of the formula Ia.9 in which R^(10b) is 6-chloropyridin-3-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 237

Compounds of the formula Ia.9 in which R^(10b) is 2-methoxypyridin-3-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 238

Compounds of the formula Ia.9 in which R^(10b) is 4-methoxypyridin-3-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 239

Compounds of the formula Ia.9 in which R^(10b) is 5-methoxypyridin-3-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 240

Compounds of the formula Ia.9 in which R^(10b) is 6-methoxypyridin-3-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 241

Compounds of the formula Ia.9 in which R^(10b) is pyridin-4-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 242

Compounds of the formula Ia.9 in which R^(10b) is 2-chloropyridin-4-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 243

Compounds of the formula Ia.9 in which R^(10b) is 3-chloropyridin-4-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 244

Compounds of the formula Ia.9 in which R^(10b) is 2-methoxypyridin-4-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 245

Compounds of the formula Ia.9 in which R^(10b) is 3-methoxypyridin-4-yl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 246

Compounds of the formula Ia.9 in which R^(10b) is pyrimidin-2-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 247

Compounds of the formula Ia.9 in which R^(10b) is pyrimidin-4-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 248

Compounds of the formula Ia.9 in which R^(10b) is pyrimidin-5-yl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 249

Compounds of the formula Ia.9 in which R^(10b) is pyrrol-2-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 250

Compounds of the formula Ia.9 in which R^(10b) is pyrrol-3-yl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 251

Compounds of the formula Ia.9 in which R^(10b) is hydrogen, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 252

Compounds of the formula Ia.9 in which R^(10b) is methyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 253

Compounds of the formula Ia.9 in which R^(10b) is ethyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 254

Compounds of the formula Ia.9 in which R^(10b) is isopropyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 255

Compounds of the formula Ia.9 in which R^(10b) is methylcarbonyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 256

Compounds of the formula Ia.9 in which R^(10b) is ethylcarbonyl, and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 257

Compounds of the formula Ia.9 in which R^(10b) is isopropylcarbonyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 258

Compounds of the formula Ia.9 in which R^(10b) is methoxycarbonyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 259

Compounds of the formula Ia.9 in which R^(10b) is ethoxycarbonyl, andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 260

Compounds of the formula Ia.9 in which R^(10b) is isopropoxycarbonyl,and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Tables 261 to 320

Compounds of the formula Ia.10 in which R^(10b) is as defined in any oftables 201 to 260 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Tables 321 to 380

Compounds of the formula Ia.11 in which R^(10b) is as defined in any oftables 201 to 260 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Tables 381 to 440

Compounds of the formula Ia.12 in which R^(10b) is as defined in any oftables 201 to 260 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Table 441

Compounds of the formula Ia.13 in which R⁶ is hydrogen and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 442

Compounds of the formula Ia.13 in which R⁶ is methyl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 443

Compounds of the formula Ia.13 in which R⁶ is ethyl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 444

Compounds of the formula Ia.13 in which R⁶ is propyl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 445

Compounds of the formula Ia.13 in which R⁶ is isopropyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 446

Compounds of the formula Ia.13 in which R⁶ is n-butyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 447

Compounds of the formula Ia.13 in which R⁶ is sec-butyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 448

Compounds of the formula Ia.13 in which R⁶ is isobutyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 449

Compounds of the formula Ia.13 in which R⁶ is tert-butyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 450

Compounds of the formula Ia.13 in which R⁶ is CH₂—C(CH₃)₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 451

Compounds of the formula Ia.13 in which R⁶ is —CH₂CN and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 452

Compounds of the formula Ia.13 in which R⁶ is —CH₂—CH═CH₂ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 453

Compounds of the formula Ia.13 in which R⁶ is —CH₂C—CH and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 454

Compounds of the formula Ia.13 in which R⁶ is CH₂CH₂OH and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 455

Compounds of the formula Ia.13 in which R⁶ is —CH₂CH₂OCH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 456

Compounds of the formula Ia.13 in which R⁶ is —CH₂CH₂OCH₂CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 457

Compounds of the formula Ia.13 in which R⁶ is —CH₂CH₂OCF₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 458

Compounds of the formula Ia.13 in which R⁶ is —CH₂CH₂OCH₂CF₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 459

Compounds of the formula Ia.13 in which R⁶ is —CH(CH₃)CH₂OCH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 460

Compounds of the formula Ia.13 in which R⁶ is —CH(CH₃)CH₂OCH₂CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 461

Compounds of the formula Ia.13 in which R⁶ is —CH₂CH₂SCH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 462

Compounds of the formula Ia.13 in which R⁶ is —CH₂CH₂S(O)CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 463

Compounds of the formula Ia.13 in which R⁶ is —CH₂CH₂S(O)₂CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 464

Compounds of the formula Ia.13 in which R⁶ is —CH₂CH₂SCH₂CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 465

Compounds of the formula Ia.13 in which R⁶ is —CH₂CH₂S(O)CH₂CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 466

Compounds of the formula Ia.13 in which R⁶ is —CH₂CH₂S(O)₂CH₂CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 467

Compounds of the formula Ia.13 in which R⁶ is —CH(CH₃)CH₂SCH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 468

Compounds of the formula Ia.13 in which R⁶ is —CH(CH₃)CH₂S(O)CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 469

Compounds of the formula Ia.13 in which R⁶ is —CH(CH₃)CH₂S(O)₂CH₃ andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 470

Compounds of the formula Ia.13 in which R⁶ is —C(CH₃)₂CH₂SCH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 471

Compounds of the formula Ia.13 in which R⁶ is —C(CH₃)₂CH₂S(O)CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 472

Compounds of the formula Ia.13 in which R⁶ is —C(CH₃)₂CH₂S(O)₂CH₃ andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 473

Compounds of the formula Ia.13 in which R⁶ is —CH₂CH₂SCF₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 474

Compounds of the formula Ia.13 in which R⁶ is CF₃ and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 475

Compounds of the formula Ia.13 in which R⁶ is CH₂CHF₂ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 476

Compounds of the formula Ia.13 in which R⁶ is CH₂CF₃ and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 477

Compounds of the formula Ia.13 in which R⁶ is CH₂CH₂CF₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 478

Compounds of the formula Ia.13 in which R⁶ is CH(CH₃)CF₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 479

Compounds of the formula Ia.13 in which R⁶ is CH(CF₃)₂ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 480

Compounds of the formula Ia.13 in which R⁶ is CH₂CH₂CH₂CF₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 481

Compounds of the formula Ia.13 in which R⁶ is CH₂CH₂CH═CF₂ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 482

Compounds of the formula Ia.13 in which R⁶ is CH₂CH₂CF═CF₂ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 483

Compounds of the formula Ia.13 in which R⁶ is cyclopropyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 484

Compounds of the formula Ia.13 in which R⁶ is 1-cyano-cyclopropyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 485

Compounds of the formula Ia.13 in which R⁶ is1-(pyridin-2-yl)-cyclopropyl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 486

Compounds of the formula Ia.13 in which R⁶ is cyclobutyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 487

Compounds of the formula Ia.13 in which R⁶ is cyclopentyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 488

Compounds of the formula Ia.13 in which R⁶ is cyclohexyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 489

Compounds of the formula Ia.13 in which R⁶ is —CH₂-cyclopropyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 490

Compounds of the formula Ia.13 in which R⁶ is —CH₂-(1-cyano-cyclopropyl)and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 491

Compounds of the formula Ia.13 in which R⁶ is—CH₂-(2,2-difluorocyclopropyl) and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 492

Compounds of the formula Ia.13 in which R⁶ is—CH₂-(2,2-dichlorocyclopropyl) and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 493

Compounds of the formula Ia.13 in which R⁶ is —CH₂-cyclobutyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 494

Compounds of the formula Ia.13 in which R⁶ is—CH₂-(2,2-difluorocyclobutyl) and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 495

Compounds of the formula Ia.13 in which R⁶ is —CH₂-cyclopentyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 496

Compounds of the formula Ia.13 in which R⁶ is —CH₂-cyclohexyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 497

Compounds of the formula Ia.13 in which R⁶ is 1,1-difluorocyclobut-3-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 498

Compounds of the formula Ia.13 in which R⁶ is—CH₂-1,1-difluorocyclobut-3-yl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 499

Compounds of the formula Ia.13 in which R⁶ is thietan-3-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 500

Compounds of the formula Ia.13 in which R⁶ is 1-oxo-thietan-3-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 501

Compounds of the formula Ia.13 in which R⁶ is 1,1-dioxo-thietan-3-yl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 502

Compounds of the formula Ia.13 in which R⁶ is 3-methyl-thietan-3-yl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 503

Compounds of the formula Ia.13 in which R⁶ is3-methyl-1-oxo-thietan-3-yl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 504

Compounds of the formula Ia.13 in which R⁶ is3-methyl-1,1-dioxo-thietan-3-yl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 505

Compounds of the formula Ia.13 in which R⁶ is —CH₂-thietan-3-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 506

Compounds of the formula Ia.13 in which R⁶ is —CH₂-(1-oxo-thietan-3-yl)and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 507

Compounds of the formula Ia.13 in which R⁶ is—CH₂-(1,1-dioxo-thietan-3-yl) and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 508

Compounds of the formula Ia.13 in which R⁶ is tetrahydrothiophen-3-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 509

Compounds of the formula Ia.13 in which R⁶ is1-oxo-tetrahydrothiophen-3-yl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 510

Compounds of the formula Ia.13 in which R⁶ is1,1-dioxo-tetrahydrothiophen-3-yl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 511

Compounds of the formula Ia.13 in which R⁶ is phenyl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 512

Compounds of the formula Ia.13 in which R⁶ is 2-nitrophenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 513

Compounds of the formula Ia.13 in which R⁶ is pyridin-2-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 514

Compounds of the formula Ia.13 in which R⁶ is pyridin-3-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 515

Compounds of the formula Ia.13 in which R⁶ is pyridin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 516

Compounds of the formula Ia.13 in which R⁶ is pyrimidin-2-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 517

Compounds of the formula Ia.13 in which R⁶ is pyrimidin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 518

Compounds of the formula Ia.13 in which R⁶ is pyrimidin-5-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 519

Compounds of the formula Ia.13 in which R⁶ is thiazol-2-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 520

Compounds of the formula Ia.13 in which R⁶ is4-trifluoromethylthiazol-2-yl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 521

Compounds of the formula Ia.13 in which R⁶ is oxetan-3-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 522

Compounds of the formula Ia.13 in which R⁶ is tetrahydrofuran-2-yl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 523

Compounds of the formula Ia.13 in which R⁶ is tetrahydrofuran-3-yl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 524

Compounds of the formula Ia.13 in which R⁶ is 2-oxotetrahydrofuran-3-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 525

Compounds of the formula Ia.13 in which R⁶ is 2-oxopyrrolidin-3-yl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 526

Compounds of the formula Ia.13 in which R⁶ is1-methyl-2-oxopyrrolidin-3-yl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 527

Compounds of the formula Ia.13 in which R⁶ is2-oxo-1-(2,2,2-trifluoroethyl)-pyrrolidin-3-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 528

Compounds of the formula Ia.13 in which R⁶ is azetidin-3-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 529

Compounds of the formula Ia.13 in which R⁶ is 1-acetyl-azetidin-3-yl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 530

Compounds of the formula Ia.13 in which R⁶ is —NH-phenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 531

Compounds of the formula Ia.13 in which R⁶ is —NH-pyridin-2-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 532

Compounds of the formula Ia.13 in which R⁶ is —NH-pyridin-3-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 533

Compounds of the formula Ia.13 in which R⁶ is —NH-pyridin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 534

Compounds of the formula Ia.13 in which R⁶ is —N(CH₃)-pyridin-2-yl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 535

Compounds of the formula Ia.13 in which R⁶ is —NH-pyrimidin-2-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 536

Compounds of the formula Ia.13 in which R⁶ is —NH-pyrimidin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 537

Compounds of the formula Ia.13 in which R⁶ is —NH-pyrimidin-5-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 538

Compounds of the formula Ia.13 in which R⁶ is —CH₂—COOCH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 539

Compounds of the formula Ia.13 in which R⁶ is —CH₂—COO—CH₂CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 540

Compounds of the formula Ia.13 in which R⁶ is —CH₂—CONH—CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 541

Compounds of the formula Ia.13 in which R⁶ is —CH₂—CONH—CH₂CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 542

Compounds of the formula Ia.13 in which R⁶ is —CH₂—CONH—CF₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 543

Compounds of the formula Ia.13 in which R⁶ is —CH₂—CONH—CH₂CF₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 544

Compounds of the formula Ia.13 in which R⁶ is —CH₂—CONH-cyclopropyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 545

Compounds of the formula Ia.13 in which R⁶ is —CH₂—CONH-isopropyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 546

Compounds of the formula Ia.13 in which R⁶ is —CH₂—CONH—CH(CF₃)CH₃ andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 547

Compounds of the formula Ia.13 in which R⁶ is —CH₂—CONH—CH(CF₃)₂ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 548

Compounds of the formula Ia.13 in which R⁶ is —CH₂—CONH—CH₂CH₂CF₃ andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 549

Compounds of the formula Ia.13 in which R⁶ is —CH₂—CONH—CH₂CN and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 550

Compounds of the formula Ia.13 in which R⁶ is —CH₂—CONH—CH₂C—CH and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 551

Compounds of the formula Ia.13 in which R⁶ is —CH₂—CON(CH₃)—CH₂CF₃ andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 552

Compounds of the formula Ia.13 in which R⁶ is —CH(CH₃)—CONH—CH₂CF₃ andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 553

Compounds of the formula Ia.13 in which R⁶ is —CH₂—CONH—CH₂-cyclopropyland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 554

Compounds of the formula Ia.13 in which R⁶ is —CH₂—CONH-thietan-3-yl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 555

Compounds of the formula Ia.13 in which R⁶ is—CH₂—CONH-1-oxo-thietan-3-yl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 556

Compounds of the formula Ia.13 in which R⁶ is—CH₂—CONH-1,1-dioxo-thietan-3-yl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 557

Compounds of the formula Ia.13 in which R⁶ is benzyl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 558

Compounds of the formula Ia.13 in which R⁶ is 2-fluorobenzyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 559

Compounds of the formula Ia.13 in which R⁶ is 3-fluorobenzyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 560

Compounds of the formula Ia.13 in which R⁶ is 4-fluorobenzyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 561

Compounds of the formula Ia.13 in which R⁶ is 2-chlorobenzyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 562

Compounds of the formula Ia.13 in which R⁶ is 3-chlorobenzyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 563

Compounds of the formula Ia.13 in which R⁶ is 4-chlorobenzyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 564

Compounds of the formula Ia.13 in which R⁶ is 2-methoxybenzyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 565

Compounds of the formula Ia.13 in which R⁶ is 3-methoxybenzyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 566

Compounds of the formula Ia.13 in which R⁶ is 4-methoxybenzyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 567

Compounds of the formula Ia.13 in which R⁶ is 2-methylsulfanylbenzyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 568

Compounds of the formula Ia.13 in which R⁶ is 3-methylsulfanylbenzyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 569

Compounds of the formula Ia.13 in which R⁶ is 4-methylsulfanylbenzyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 570

Compounds of the formula Ia.13 in which R⁶ is 2-methylsulfonylbenzyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 571

Compounds of the formula Ia.13 in which R⁶ is 3-methylsulfonylbenzyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 572

Compounds of the formula Ia.13 in which R⁶ is 4-methylsulfonylbenzyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 573

Compounds of the formula Ia.13 in which R⁶ is pyridin-2-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 574

Compounds of the formula Ia.13 in which R⁶ is pyridin-3-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 575

Compounds of the formula Ia.13 in which R⁶ is6-chloro-pyridin-3-yl-methyl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 576

Compounds of the formula Ia.13 in which R⁶ is pyridin-4-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 577

Compounds of the formula Ia.13 in which R⁶ is5-chloro-pyridin-2-yl-methyl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 578

Compounds of the formula Ia.13 in which R⁶ is6-(trifluoromethyl)-pyridin-2-yl-methyl and the combination of R^(2a),R^(2b), R^(2c) and R⁴ for a compound corresponds in each case to one rowof Table A

Table 579

Compounds of the formula Ia.13 in which R⁶ is6-(trifluoromethyl)-pyridin-3-yl-methyl and the combination of R^(2a),R^(2b), R^(2c) and R⁴ for a compound corresponds in each case to one rowof Table A

Table 580

Compounds of the formula Ia.13 in which R⁶ is pyrimidin-2-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 581

Compounds of the formula Ia.13 in which R⁶ is pyrimidin-4-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 582

Compounds of the formula Ia.13 in which R⁶ is pyrimidin-5-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 583

Compounds of the formula Ia.13 in which R⁶ is pyridazin-3-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 584

Compounds of the formula Ia.13 in which R⁶ is pyrazin-2-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 585

Compounds of the formula Ia.13 in which R⁶ is thien-2-yl-methyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 586

Compounds of the formula Ia.13 in which R⁶ is thien-3-yl-methyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 587

Compounds of the formula Ia.13 in which R⁶ is thiazol-2-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 588

Compounds of the formula Ia.13 in which R⁶ is thiazol-4-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 589

Compounds of the formula Ia.13 in which R⁶ is thiazol-5-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 590

Compounds of the formula Ia.13 in which R⁶ is2-chloro-thiazol-5-yl-methyl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 591

Compounds of the formula Ia.13 in which R⁶ is isothiazol-3-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 592

Compounds of the formula Ia.13 in which R⁶ is isothiazol-4-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 593

Compounds of the formula Ia.13 in which R⁶ is isothiazol-5-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 594

Compounds of the formula Ia.13 in which R⁶ is oxazol-2-yl-methyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 595

Compounds of the formula Ia.13 in which R⁶ is oxazol-4-yl-methyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 596

Compounds of the formula Ia.13 in which R⁶ is oxazol-5-yl-methyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 597

Compounds of the formula Ia.13 in which R⁶ is isoxazol-3-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 598

Compounds of the formula Ia.13 in which R⁶ is isoxazol-4-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 599

Compounds of the formula Ia.13 in which R⁶ is isoxazol-5-yl-methyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 600

Compounds of the formula Ia.13 in which R⁶ is[1,2,3]-thiadiazol-4-yl-methyl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 601

Compounds of the formula Ia.13 in which R⁶ is[1,3,4]-thiadiazol-2-yl-methyl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 602

Compounds of the formula Ia.13 in which R⁶ is1-methyl-imidazol-2-yl-methyl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 603

Compounds of the formula Ia.13 in which R⁶ is1-methyl-imidazol-4-yl-methyl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 604

Compounds of the formula Ia.13 in which R⁶ is1-methyl-imidazol-5-yl-methyl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 605

Compounds of the formula Ia.13 in which R⁶ is1-methyl-pyrazol-3-yl-methyl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 606

Compounds of the formula Ia.13 in which R⁶ is2-methyl-pyrazol-3-yl-methyl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 607

Compounds of the formula Ia.13 in which R⁶ istetrahydrofuran-3-yl-methyl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 608

Compounds of the formula Ia.13 in which R⁶ is 1,3-dioxolan-2-yl-methyland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 609

Compounds of the formula Ia.13 in which R⁶ is 2-pyridyl-eth-1-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 610

Compounds of the formula Ia.13 in which R⁶ is (1R)-2-pyridyl-eth-1-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 611

Compounds of the formula Ia.13 in which R⁶ is (1S)-2-pyridyl-eth-1-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 612

Compounds of the formula Ia.13 in which R⁶ is —CONH₂ and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 613

Compounds of the formula Ia.13 in which R⁶ is —CONH—CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 614

Compounds of the formula Ia.13 in which R⁶ is —CONH—CH₂CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 615

Compounds of the formula Ia.13 in which R⁶ is —CONH—CH₂CH₂CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 616

Compounds of the formula Ia.13 in which R⁶ is —CONH-cyclopropyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 617

Compounds of the formula Ia.13 in which R⁶ is —CONH—CH₂-cyclopropyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 618

Compounds of the formula Ia.13 in which R⁶ is —CONH-phenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 619

Compounds of the formula Ia.13 in which R⁶ is —CONH-benzyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 620

Compounds of the formula Ia.13 in which R⁶ is —NHCO—NH—CH₂CF₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 621

Compounds of the formula Ia.13 in which R⁶ is —NHCO—NH—CH₂CHF₂ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 622

Compounds of the formula Ia.13 in which R⁶ is —CH═NOCH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 623

Compounds of the formula Ia.13 in which R⁶ is —CH═NOCH₂CF₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 624

Compounds of the formula Ia.13 in which R⁶ is 3-oxo-isoxazolidin-4-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 625

Compounds of the formula Ia.13 in which R⁶ is2-methyl-3-oxo-isoxazolidin-4-yl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 626

Compounds of the formula Ia.13 in which R⁶ is2-ethyl-3-oxo-isoxazolidin-4-yl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 627

Compounds of the formula Ia.13 in which R⁶ is2-propyl-3-oxo-isoxazolidin-4-yl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 628

Compounds of the formula Ia.13 in which R⁶ is2-butyl-3-oxo-isoxazolidin-4-yl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 629

Compounds of the formula Ia.13 in which R⁶ is2-(but-2-yl)-3-oxo-isoxazolidin-4-yl and the combination of R^(2a),R^(2b), R^(2c) and R⁴ for a compound corresponds in each case to one rowof Table A

Table 630

Compounds of the formula Ia.13 in which R⁶ is2-(3-bromopropyl)-3-oxo-isoxazolidin-4-yl and the combination of R^(2a),R^(2b), R^(2c) and R⁴ for a compound corresponds in each case to one rowof Table A

Table 631

Compounds of the formula Ia.13 in which R⁶ is2-(2-fluoroethyl)-3-oxo-isoxazolidin-4-yl and the combination of R^(2a),R^(2b), R^(2c) and R⁴ for a compound corresponds in each case to one rowof Table A

Table 632

Compounds of the formula Ia.13 in which R⁶ is2-(2,2-difluoroethyl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 633

Compounds of the formula Ia.13 in which R⁶ is2-(2,2,2-trifluoroethyl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 634

Compounds of the formula Ia.13 in which R⁶ is2-(3,3,3-trifluoropropyl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 635

Compounds of the formula Ia.13 in which R⁶ is2-(2-methoxyethyl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 636

Compounds of the formula Ia.13 in which R⁶ is2-(1-methoxy-prop-2-yl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 637

Compounds of the formula Ia.13 in which R⁶ is2-cyclobutyl-3-oxo-isoxazolidin-4-yl and the combination of R^(2a),R^(2b), R^(2c) and R⁴ for a compound corresponds in each case to one rowof Table A

Table 638

Compounds of the formula Ia.13 in which R⁶ is2-(2-methylcyclohex-1-yl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 639

Compounds of the formula Ia.13 in which R⁶ is2-(phenylmethyl)-3-oxo-isoxazolidin-4-yl and the combination of R^(2a),R^(2b), R^(2c) and R⁴ for a compound corresponds in each case to one rowof Table A

Table 640

Compounds of the formula Ia.13 in which R⁶ is2-(1-phenyl-eth-1-yl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 641

Compounds of the formula Ia.13 in which R⁶ is2-(2-phenyl-eth-1-yl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 642

Compounds of the formula Ia.13 in which R⁶ is2-[(3-chlorophenyl)-methyl]-3-oxo-isoxazolidin-4-yl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 643

Compounds of the formula Ia.13 in which R⁶ is2-[(2-fluorophenyl)-methyl]-3-oxo-isoxazolidin-4-yl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 644

Compounds of the formula Ia.13 in which R⁶ is2-[(4-methoxyphenyl)-methyl]-3-oxo-isoxazolidin-4-yl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 645

Compounds of the formula Ia.13 in which R⁶ is2-[(2-trifluoromethylphenyl)-methyl]-3-oxo-isoxazolidin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 646

Compounds of the formula Ia.13 in which R⁶ is2-[(2-trifluoromethoxyphenyl)-methyl]-3-oxo-isoxazolidin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 647

Compounds of the formula Ia.13 in which R⁶ is2-(pyridin-2-yl-methyl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 648

Compounds of the formula Ia.13 in which R⁶ is2-(pyridin-3-yl-methyl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 649

Compounds of the formula Ia.13 in which R⁶ is2-[(2-chloropyridin-5-yl)-methyl]-3-oxo-isoxazolidin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 650

Compounds of the formula Ia.13 in which R⁶ is2-[(1-methyl-1H-imidazol-4-yl)-methyl]-3-oxo-isoxazolidin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 651

Compounds of the formula Ia.13 in which R⁶ is2-[(furan-2-yl)-methyl]-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 652

Compounds of the formula Ia.13 in which R⁶ is2-[(2-thiophen-2′-yl)-eth-1-yl]-3-oxo-isoxazolidin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 653

Compounds of the formula Ia.13 in which R⁶ is2-[2-(indol-3′-yl)-eth-1-yl]-3-oxo-isoxazolidin-4-yl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 654

Compounds of the formula Ia.13 in which R⁶ is2-[(1H-benzimidazol-2-yl)-methyl]-3-oxo-isoxazolidin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 655

Compounds of the formula Ia.13 in which R⁶ is2-[(oxetan-2-yl)-methyl]-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 656

Compounds of the formula Ia.13 in which R⁶ is2-[(tetrahydrofuran-2-yl)-methyl]-3-oxo-isoxazolidin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 657

Compounds of the formula Ia.13 in which R⁶ is2-[(2-[1′,3′]dioxolan-2′-yl)-eth-1-yl]-3-oxo-isoxazolidin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 658

Compounds of the formula Ia.13 in which R⁶ is2-[(2-morpholin-4′-yl)-eth-1-yl]-3-oxo-isoxazolidin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 659

Compounds of the formula Ia.13 in which R⁶ is2-[(2-benzo[1′,3′]dioxol-5′-yl)-eth-1-yl]-3-oxo-isoxazolidin-4-yl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 660

Compounds of the formula Ia.13 in which R⁶ is2-[(2,3-dihydro-benzo[1,4]dioxin-6-yl)methyl]-3-oxo-isoxazolidin-4-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 661

Compounds of the formula Ia.13 in which R⁶ is2-(2-chlorophenyl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 662

Compounds of the formula Ia.13 in which R⁶ is2-(3-fluorophenyl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 663

Compounds of the formula Ia.13 in which R⁶ is2-(2-methylphenyl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 664

Compounds of the formula Ia.13 in which R⁶ is2-(2-chloro-6-methylphenyl)-3-oxo-isoxazolidin-4-yl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 665

Compounds of the formula Ia.13 in which R⁶ is2-(2-trifluoromethylphenyl)-3-oxo-isoxazolidin-4-yl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 666

Compounds of the formula Ia.13 in which R⁶ is2-(2,4-dimethoxyphenyl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 667

Compounds of the formula Ia.13 in which R⁶ is2-(3-methylpyrid-2-yl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 668

Compounds of the formula Ia.13 in which R⁶ is2-(1,3-dimethyl-1H-pyrazol-5-yl)-3-oxo-isoxazolidin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 669

Compounds of the formula Ia.13 in which R⁶ is2-(4-methylthiazol-2-yl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 670

Compounds of the formula Ia.13 in which R⁶ is2-(5-methylthiadiazol-2-yl)-3-oxo-isoxazolidin-4-yl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 671

Compounds of the formula Ia.13 in which R⁶ is2-(quinolin-2-yl)-3-oxo-isoxazolidin-4-yl and the combination of R^(2a),R^(2b), R^(2c) and R⁴ for a compound corresponds in each case to one rowof Table A

Table 672

Compounds of the formula Ia.13 in which R⁶ is2-(quinolin-5-yl)-3-oxo-isoxazolidin-4-yl and the combination of R^(2a),R^(2b), R^(2c) and R⁴ for a compound corresponds in each case to one rowof Table A

Table 673

Compounds of the formula Ia.13 in which R⁶ is2-(benzothiazol-6-yl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 674

Compounds of the formula Ia.13 in which R⁶ is2-(4-methylbenzothiazol-2-yl)-3-oxo-isoxazolidin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 675

Compounds of the formula Ia.13 in which R⁶ is2-(thietan-3-yl)-3-oxo-isoxazolidin-4-yl and the combination of R^(2a),R^(2b), R^(2c) and R⁴ for a compound corresponds in each case to one rowof Table A

Table 676

Compounds of the formula Ia.13 in which R⁶ is2-(1-oxo-thietan-3-yl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 677

Compounds of the formula Ia.13 in which R⁶ is2-(1,1-dioxo-thietan-3-yl)-3-oxo-isoxazolidin-4-yl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 678

Compounds of the formula Ia.13 in which R⁶ is2-(3-methylthietan-3-yl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 679

Compounds of the formula Ia.13 in which R⁶ is2-(oxetan-3-yl)-3-oxo-isoxazolidin-4-yl and the combination of R^(2a),R^(2b), R^(2c) and R⁴ for a compound corresponds in each case to one rowof Table A

Table 680

Compounds of the formula Ia.13 in which R⁶ is2-(tetrahydropyran-4-yl)-3-oxo-isoxazolidin-4-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Tables 681 to 920

Compounds of the formula Ia.14 in which R⁶ is as defined in any oftables 441 to 680 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Tables 921 to 1160

Compounds of the formula Ia.15 in which R⁶ is as defined in any oftables 441 to 680 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Tables 1161 to 1400

Compounds of the formula Ia.16 in which R⁶ is as defined in any oftables 441 to 680 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Table 1401

Compounds of the formula Ia.17 in which R⁸ is methyl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 1402

Compounds of the formula Ia.17 in which R⁸ is ethyl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 1403

Compounds of the formula Ia.17 in which R⁸ is propyl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 1404

Compounds of the formula Ia.17 in which R⁸ is isopropyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1405

Compounds of the formula Ia.17 in which R⁸ is n-butyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1406

Compounds of the formula Ia.17 in which R⁸ is sec-butyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1407

Compounds of the formula Ia.17 in which R⁸ is isobutyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1408

Compounds of the formula Ia.17 in which R⁸ is tert-butyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1409

Compounds of the formula Ia.17 in which R⁸ is CF₃ and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 1410

Compounds of the formula Ia.17 in which R⁸ is CH₂CHF₂ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1411

Compounds of the formula Ia.17 in which R⁸ is CH₂CF₃ and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 1412

Compounds of the formula Ia.17 in which R⁸ is CH₂CH₂CF₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1413

Compounds of the formula Ia.17 in which R⁸ is cyclopropyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1414

Compounds of the formula Ia.17 in which R⁸ is methylthiomethyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1415

Compounds of the formula Ia.17 in which R⁸ is ethylthiomethyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1416

Compounds of the formula Ia.17 in which R⁸ is methylsulfinylmethyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 1417

Compounds of the formula Ia.17 in which R⁸ is ethylsulfinylmethyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 1418

Compounds of the formula Ia.17 in which R⁸ is methylsulfonylmethyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 1419

Compounds of the formula Ia.17 in which R⁸ is ethylsulfonylmethyl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 1420

Compounds of the formula Ia.17 in which R⁸ is phenyl and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 1421

Compounds of the formula Ia.17 in which R⁸ is 2-fluorophenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1422

Compounds of the formula Ia.17 in which R⁸ is 3-fluorophenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1423

Compounds of the formula Ia.17 in which R⁸ is 4-fluorophenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1424

Compounds of the formula Ia.17 in which R⁸ is 2,3-difluorophenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1425

Compounds of the formula Ia.17 in which R⁸ is 2,4-difluorophenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1426

Compounds of the formula Ia.17 in which R⁸ is 2,5-difluorophenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1427

Compounds of the formula Ia.17 in which R⁸ is 2,6-difluorophenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1428

Compounds of the formula Ia.17 in which R⁸ is 3,4-difluorophenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1429

Compounds of the formula Ia.17 in which R⁸ is 3,5-difluorophenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1430

Compounds of the formula Ia.17 in which R⁸ is 2-chlorophenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1431

Compounds of the formula Ia.17 in which R⁸ is 3-chlorophenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1432

Compounds of the formula Ia.17 in which R⁸ is 4-chlorophenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1433

Compounds of the formula Ia.17 in which R⁸ is 2-methoxyphenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1434

Compounds of the formula Ia.17 in which R⁸ is 3-methoxyphenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1435

Compounds of the formula Ia.17 in which R⁸ is 4-methoxyphenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1436

Compounds of the formula Ia.17 in which R⁸ is thietan-3-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1437

Compounds of the formula Ia.17 in which R⁸ is 1-oxo-thietan-3-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1438

Compounds of the formula Ia.17 in which R⁸ is 1,1-dioxo-thietan-3-yl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 1439

Compounds of the formula Ia.17 in which R⁸ is pyridin-2-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1440

Compounds of the formula Ia.17 in which R⁸ is pyridin-3-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1441

Compounds of the formula Ia.17 in which R⁸ is pyridin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1442

Compounds of the formula Ia.17 in which R⁸ is 4-chloropyridin-3-yl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 1443

Compounds of the formula Ia.17 in which R⁸ is —NH—CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1444

Compounds of the formula Ia.17 in which R⁸ is —NH—CH₂CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1445

Compounds of the formula Ia.17 in which R⁸ is —NH—CH₂CH₂CH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1446

Compounds of the formula Ia.17 in which R⁸ is —NH—CF₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1447

Compounds of the formula Ia.17 in which R⁸ is —NH—CH₂CHF₂ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1448

Compounds of the formula Ia.17 in which R⁸ is —NH—CH₂CF₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1449

Compounds of the formula Ia.17 in which R⁸ is —NH-phenyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 1450

Compounds of the formula Ia.17 in which R⁸ is —NH-benzyl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Tables 1451 to 1500

Compounds of the formula Ia.18 in which R⁸ is as defined in any oftables 1401 to 1450 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Tables 1501 to 1550

Compounds of the formula Ia.19 in which R⁸ is as defined in any oftables 1401 to 1450 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Tables 1551 to 1600

Compounds of the formula Ia.20 in which R⁸ is as defined in any oftables 1401 to 1450 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Tables 1601 to 1650

Compounds of the formula Ia.21 in which R⁸ is as defined in any oftables 1401 to 1450 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Tables 1651 to 1700

Compounds of the formula Ia.22 in which R⁸ is as defined in any oftables 1401 to 1450 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Tables 1701 to 1750

Compounds of the formula Ia.23 in which R⁸ is as defined in any oftables 1401 to 1450 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Tables 1751 to 1800

Compounds of the formula Ia.24 in which R⁸ is as defined in any oftables 1401 to 1450 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Tables 1801 to 1850

Compounds of the formula Ia.25 in which R⁸ is as defined in any oftables 1401 to 1450 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Tables 1851 to 1900

Compounds of the formula Ia.26 in which R⁸ is as defined in any oftables 1401 to 1450 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Tables 1901 to 1950

Compounds of the formula Ia.27 in which R⁸ is as defined in any oftables 1401 to 1450 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Tables 1951 to 2000

Compounds of the formula Ia.28 in which R⁸ is as defined in any oftables 1401 to 1450 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Table 2001

Compounds of the formula Ia.29 in which A⁴ is 1H-pyrrol-1-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2002

Compounds of the formula Ia.29 in which A⁴ is 1H-3-chloro-pyrrol-1-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2003

Compounds of the formula Ia.29 in which A⁴ is 1H-3-cyano-pyrrol-1-yl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2004

Compounds of the formula Ia.29 in which A⁴ is 1H-pyrazol-1-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2005

Compounds of the formula Ia.29 in which A⁴ is 1H-4-cloro-pyrazol-1-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2006

Compounds of the formula Ia.29 in which A⁴ is 1H-4-cyano-pyrazol-1-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2007

Compounds of the formula Ia.29 in which A⁴ is 1H-imidazol-1-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2008

Compounds of the formula Ia.29 in which A⁴ is 1H-4-chloro-imidazol-1-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2009

Compounds of the formula Ia.29 in which A⁴ is 1H-4-cyano-imidazol-1-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2010

Compounds of the formula Ia.29 in which A⁴ is 1H-[1,2,4]-triazol-1-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2011

Compounds of the formula Ia.29 in which A⁴ is1H-[1,2,4]-3-chloro-triazol-1-yl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 2012

Compounds of the formula Ia.29 in which A⁴ is1H-[1,2,4]-3-cyano-triazol-1-yl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 2013

Compounds of the formula Ia.29 in which A⁴ is 1H-1-methyl-pyrrol-2-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2014

Compounds of the formula Ia.29 in which A⁴ is 1H-1-methyl-pyrrol-3-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2015

Compounds of the formula Ia.29 in which A⁴ is 1H-1-methyl-pyrazol-4-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2016

Compounds of the formula Ia.29 in which A⁴ is 1H-1-methyl-pyrazol-5-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2017

Compounds of the formula Ia.29 in which A⁴ is1H-1,3-dimethyl-pyrazol-5-yl and the combination of R^(2a), R^(2b),R^(2c) and R⁴ for a compound corresponds in each case to one row ofTable A

Table 2018

Compounds of the formula Ia.29 in which A⁴ is1H-1-methyl-3-trifluoromethyl-pyrazol-5-yl and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 2019

Compounds of the formula Ia.29 in which A⁴ is 1H-1-[1,2,3]-triazol-5-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2020

Compounds of the formula Ia.29 in which A⁴ is pyridin-2-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2021

Compounds of the formula Ia.29 in which A⁴ is pyridin-3-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2022

Compounds of the formula Ia.29 in which A⁴ is pyridin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2023

Compounds of the formula Ia.29 in which A⁴ is pyrimidin-2-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2024

Compounds of the formula Ia.29 in which A⁴ is pyrimidin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2025

Compounds of the formula Ia.29 in which A⁴ is pyrimidin-5-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2026

Compounds of the formula Ia.29 in which A⁴ is pyrazin-2-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Tables 2027 to 2052

Compounds of the formula Ia.30 in which A⁴ is as defined in any oftables 2001 to 2026 and the combination of R^(2a), R^(2b), R^(2c) and R⁴for a compound corresponds in each case to one row of Table A

Table 2053

Compounds of the formula Ia.31 in which Y is H and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 2054

Compounds of the formula Ia.31 in which Y is OH and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 2055

Compounds of the formula Ia.31 in which Y is OCH₃ and the combination ofR^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each case toone row of Table A

Table 2056

Compounds of the formula Ia.31 in which Y is OC₂H₅ and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 2057

Compounds of the formula Ia.31 in which Y is OC(CH₃)₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2058

Compounds of the formula Ia.31 in which Y is OCH₂CF₃ and the combinationof R^(2a), R^(2b), R^(2c) and R⁴ for a compound corresponds in each caseto one row of Table A

Table 2059

Compounds of the formula Ia.31 in which Y is OCH₂CH₂CF₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2060

Compounds of the formula Ia.31 in which Y is OCH₂-(pyridine-2-yl) andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2061

Compounds of the formula Ia.31 in which Y is aziridin-1-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2062

Compounds of the formula Ia.31 in which Y is azetidin-1-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2063

Compounds of the formula Ia.31 in which Y is pyrrolidin-1-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2064

Compounds of the formula Ia.31 in which Y is piperidin-1-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2065

Compounds of the formula Ia.31 in which Y is morpholin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2066

Compounds of the formula Ia.31 in which Y is thiomorpholin-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2067

Compounds of the formula Ia.31 in which Y is thiazinan-4-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2068

Compounds of the formula Ia.31 in which Y is 1-oxo-thiazinan-4-yl andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2069

Compounds of the formula Ia.31 in which Y is 1,1-dioxo-thiazinan-4-yland the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2070

Compounds of the formula Ia.31 in which Y is thiazolidin-3-yl and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2071

Compounds of the formula Ia.31 in which Y is —N═S(CH₃)₂ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2072

Compounds of the formula Ia.31 in which Y is —N═S(C₂H₅)₂ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2073

Compounds of the formula Ia.31 in which Y is —N═S[CH(CH₃)₂]₂ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

Table 2074

Compounds of the formula Ia.31 in which Y is —N(CH₃)—CH₂— (thiazol-4-yl)and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2075

Compounds of the formula Ia.31 in which Y is —N(C₂H₅)—CH₂—(thiazol-4-yl) and the combination of R^(2a), R^(2b), R^(2c) and R⁴ fora compound corresponds in each case to one row of Table A

Table 2076

Compounds of the formula Ia.31 in which Y is —N(CH₃)—CH₂— (pyridin-2-yl)and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2077

Compounds of the formula Ia.31 in which Y is —N(C₂H₅)—CH₂—(pyridin-2-yl) and the combination of R^(2a), R^(2b), R^(2c) and R⁴ fora compound corresponds in each case to one row of Table A

Table 2078

Compounds of the formula Ia.31 in which Y is —N(CH₂CN)—CH₂—(pyridin-2-yl) and the combination of R^(2a), R^(2b), R^(2c) and R⁴ fora compound corresponds in each case to one row of Table A

Table 2079

Compounds of the formula Ia.31 in which Y is —N(CH₂—C—CH)—CH₂—(pyridin-2-yl) and the combination of R^(2a), R^(2b), R^(2c) and R⁴ fora compound corresponds in each case to one row of Table A

Table 2080

Compounds of the formula Ia.31 in which Y is —N(CH₃)—CH₂—CONH—CH₂CF₃ andthe combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2081

Compounds of the formula Ia.31 in which Y is —N(C₂H₅)—CH₂—CONH—CH₂CF₃and the combination of R^(2a), R^(2b), R^(2c) and R⁴ for a compoundcorresponds in each case to one row of Table A

Table 2082

Compounds of the formula Ia.31 in which Y is —N(CH₃)—OCH₃ and thecombination of R^(2a), R^(2b), R^(2c) and R⁴ for a compound correspondsin each case to one row of Table A

TABLE A No. R^(2a) R^(2b) R^(2c) R⁴ A-1 F H F H A-2 F F F H A-3 F Cl F HA-4 F Br F H A-5 F H Cl H A-6 F H Br H A-7 Cl H Cl H A-8 Cl Cl Cl H A-9Cl F Cl H A-10 Cl Br Cl H A-11 Cl H Br H A-12 Br H Br H A-13 Br F Br HA-14 Br Cl Br H A-15 CF₃ H F H A-16 CF₃ H Cl H A-17 CF₃ H Br H A-18 CF₃H CF₃ H A-19 CF₃ F F H A-20 CF₃ Cl Cl H A-21 CF₃ Br Br H A-22 SF₅ H F HA-23 SF₅ H Cl H A-24 SF₅ H Br H A-25 SF₅ H CF₃ H A-26 F H F CH₃ A-27 F FF CH₃ A-28 F Cl F CH₃ A-29 F Br F CH₃ A-30 F H Cl CH₃ A-31 F H Br CH₃A-32 Cl H Cl CH₃ A-33 Cl Cl Cl CH₃ A-34 Cl F Cl CH₃ A-35 Cl Br Cl CH₃A-36 Cl H Br CH₃ A-37 Br H Br CH₃ A-38 Br F Br CH₃ A-39 Br Cl Br CH₃A-40 CF₃ H F CH₃ A-41 CF₃ H Cl CH₃ A-42 CF₃ H Br CH₃ A-43 CF₃ H CF₃ CH₃A-44 CF₃ F F CH₃ A-45 CF₃ Cl Cl CH₃ A-46 CF₃ Br Br CH₃ A-47 SF₅ H F CH₃A-48 SF₅ H Cl CH₃ A-49 SF₅ H Br CH₃ A-50 SF₅ H CF₃ CH₃ A-51 F H F CH₂CH₃A-52 F F F CH₂CH₃ A-53 F Cl F CH₂CH₃ A-54 F Br F CH₂CH₃ A-55 F H ClCH₂CH₃ A-56 F H Br CH₂CH₃ A-57 Cl H Cl CH₂CH₃ A-58 Cl Cl Cl CH₂CH₃ A-59Cl F Cl CH₂CH₃ A-60 Cl Br Cl CH₂CH₃ A-61 Cl H Br CH₂CH₃ A-62 Br H BrCH₂CH₃ A-63 Br F Br CH₂CH₃ A-64 Br Cl Br CH₂CH₃ A-65 CF₃ H F CH₂CH₃ A-66CF₃ H Cl CH₂CH₃ A-67 CF₃ H Br CH₂CH₃ A-68 CF₃ H CF₃ CH₂CH₃ A-69 CF₃ F FCH₂CH₃ A-70 CF₃ Cl Cl CH₂CH₃ A-71 CF₃ Br Br CH₂CH₃ A-72 SF₅ H F CH₂CH₃A-73 SF₅ H Cl CH₂CH₃ A-74 SF₅ H Br CH₂CH₃ A-75 SF₅ H CF₃ CH₂CH₃ A-76 F HF CH(CH₃)₂ A-77 F F F CH(CH₃)₂ A-78 F Cl F CH(CH₃)₂ A-79 F Br F CH(CH₃)₂A-80 F H Cl CH(CH₃)₂ A-81 F H Br CH(CH₃)₂ A-82 Cl H Cl CH(CH₃)₂ A-83 ClCl Cl CH(CH₃)₂ A-84 Cl F Cl CH(CH₃)₂ A-85 Cl Br Cl CH(CH₃)₂ A-86 Cl H BrCH(CH₃)₂ A-87 Br H Br CH(CH₃)₂ A-88 Br F Br CH(CH₃)₂ A-89 Br Cl BrCH(CH₃)₂ A-90 CF₃ H F CH(CH₃)₂ A-91 CF₃ H Cl CH(CH₃)₂ A-92 CF₃ H BrCH(CH₃)₂ A-93 CF₃ H CF₃ CH(CH₃)₂ A-94 CF₃ F F CH(CH₃)₂ A-95 CF₃ Cl ClCH(CH₃)₂ A-96 CF₃ Br Br CH(CH₃)₂ A-97 SF₅ H F CH(CH₃)₂ A-98 SF₅ H ClCH(CH₃)₂ A-99 SF₅ H Br CH(CH₃)₂ A-100 SF₅ H CF₃ CH(CH₃)₂ A-101 F H FCHF₂ A-102 F F F CHF₂ A-103 F Cl F CHF₂ A-104 F Br F CHF₂ A-105 F H ClCHF₂ A-106 F H Br CHF₂ A-107 Cl H Cl CHF₂ A-108 Cl Cl Cl CHF₂ A-109 Cl FCl CHF₂ A-110 Cl Br Cl CHF₂ A-111 Cl H Br CHF₂ A-112 Br H Br CHF₂ A-113Br F Br CHF₂ A-114 Br Cl Br CHF₂ A-115 CF₃ H F CHF₂ A-116 CF₃ H Cl CHF₂A-117 CF₃ H Br CHF₂ A-118 CF₃ H CF₃ CHF₂ A-119 CF₃ F F CHF₂ A-120 CF₃ ClCl CHF₂ A-121 CF₃ Br Br CHF₂ A-122 SF₅ H F CHF₂ A-123 SF₅ H Cl CHF₂A-124 SF₅ H Br CHF₂ A-125 SF₅ H CF₃ CHF₂ A-126 F H F CF₃ A-127 F F F CF₃A-128 F Cl F CF₃ A-129 F Br F CF₃ A-130 F H Cl CF₃ A-131 F H Br CF₃A-132 Cl H Cl CF₃ A-133 Cl Cl Cl CF₃ A-134 Cl F Cl CF₃ A-135 Cl Br ClCF₃ A-136 Cl H Br CF₃ A-137 Br H Br CF₃ A-138 Br F Br CF₃ A-139 Br Cl BrCF₃ A-140 CF₃ H F CF₃ A-141 CF₃ H Cl CF₃ A-142 CF₃ H Br CF₃ A-143 CF₃ HCF₃ CF₃ A-144 CF₃ F F CF₃ A-145 CF₃ Cl Cl CF₃ A-146 CF₃ Br Br CF₃ A-147SF₅ H F CF₃ A-148 SF₅ H Cl CF₃ A-149 SF₅ H Br CF₃ A-150 SF₃ H CF₃ CF₃A-151 F H F CH₂—CH═CH₂ A-152 F F F CH₂—CH═CH₂ A-153 F Cl F CH₂—CH═CH₂A-154 F Br F CH₂—CH═CH₂ A-155 F H Cl CH₂—CH═CH₂ A-156 F H Br CH₂—CH═CH₂A-157 Cl H Cl CH₂—CH═CH₂ A-158 Cl Cl Cl CH₂—CH═CH₂ A-159 Cl F ClCH₂—CH═CH₂ A-160 Cl Br Cl CH₂—CH═CH₂ A-161 Cl H Br CH₂—CH═CH₂ A-162 Br HBr CH₂—CH═CH₂ A-163 Br F Br CH₂—CH═CH₂ A-164 Br Cl Br CH₂—CH═CH₂ A-165CF₃ H F CH₂—CH═CH₂ A-166 CF₃ H Cl CH₂—CH═CH₂ A-167 CF₃ H Br CH₂—CH═CH₂A-168 CF₃ H CF₃ CH₂—CH═CH₂ A-169 CF₃ F F CH₂—CH═CH₂ A-170 CF₃ Cl ClCH₂—CH═CH₂ A-171 CF₃ Br Br CH₂—CH═CH₂ A-172 SF₅ H F CH₂—CH═CH₂ A-173 SF₅H Cl CH₂—CH═CH₂ A-174 SF₅ H Br CH₂—CH═CH₂ A-175 SF₅ H CF₃ CH₂—CH═CH₂A-176 F H F CH═CH₂ A-177 F F F CH═CH₂ A-178 F Cl F CH═CH₂ A-179 F Br FCH═CH₂ A-180 F H Cl CH═CH₂ A-181 F H Br CH═CH₂ A-182 Cl H Cl CH═CH₂A-183 Cl Cl Cl CH═CH₂ A-184 Cl F Cl CH═CH₂ A-185 Cl Br Cl CH═CH₂ A-186Cl H Br CH═CH₂ A-187 Br H Br CH═CH₂ A-188 Br F Br CH═CH₂ A-189 Br Cl BrCH═CH₂ A-190 CF₃ H F CH═CH₂ A-191 CF₃ H Cl CH═CH₂ A-192 CF₃ H Br CH═CH₂A-193 CF₃ H CF₃ CH═CH₂ A-194 CF₃ F F CH═CH₂ A-195 CF₃ Cl Cl CH═CH₂ A-196CF₃ Br Br CH═CH₂ A-197 SF₅ H F CH═CH₂ A-198 SF₅ H Cl CH═CH₂ A-199 SF₅ HBr CH═CH₂ A-200 SF₅ H CF₃ CH═CH₂ A-201 F H F C≡CH A-202 F F F C≡CH A-203F Cl F C≡CH A-204 F Br F C≡CH A-205 F H Cl C≡CH A-206 F H Br C≡CH A-207Cl H Cl C≡CH A-208 Cl Cl Cl C≡CH A-209 Cl F Cl C≡CH A-210 Cl Br Cl C≡CHA-211 Cl H Br C≡CH A-212 Br H Br C≡CH A-213 Br F Br C≡CH A-214 Br Cl BrC≡CH A-215 CF₃ H F C≡CH A-216 CF₃ H Cl C≡CH A-217 CF₃ H Br C≡CH A-218CF₃ H CF₃ C≡CH A-219 CF₃ F F C≡CH A-220 CF₃ Cl Cl C≡CH A-221 CF₃ Br BrC≡CH A-222 SF₅ H F C≡CH A-223 SF₅ H Cl C≡CH A-224 SF₅ H Br C≡CH A-225SF₅ H CF₃ C≡CH A-226 F H F ^(c)C₃H₅* A-227 F F F ^(c)C₃H₅* A-228 F Cl F^(c)C₃H₅* A-229 F Br F ^(c)C₃H₅* A-230 F H Cl ^(c)C₃H₅* A-231 F H Br^(c)C₃H₅* A-232 Cl H Cl ^(c)C₃H₅* A-233 Cl Cl Cl ^(c)C₃H₅* A-234 Cl F Cl^(c)C₃H₅* A-235 Cl Br Cl ^(c)C₃H₅* A-236 Cl H Br ^(c)C₃H₅* A-237 Br H Br^(c)C₃H₅* A-238 Br F Br ^(c)C₃H₅* A-239 Br Cl Br ^(c)C₃H₅* A-240 CF₃ H F^(c)C₃H₅* A-241 CF₃ H Cl ^(c)C₃H₅* A-242 CF₃ H Br ^(c)C₃H₅* A-243 CF₃ HCF₃ ^(c)C₃H₅* A-244 CF₃ F F ^(c)C₃H₅* A-245 CF₃ Cl Cl ^(c)C₃H₅* A-246CF₃ Br Br ^(c)C₃H₅* A-247 SF₅ H F ^(c)C₃H₅* A-248 SF₅ H Cl ^(c)C₃H₅*A-249 SF₅ H Br ^(c)C₃H₅* A-250 SF₅ H CF₃ ^(c)C₃H₅* A-251 F H F F A-252 FF F F A-253 F Cl F F A-254 F Br F F A-255 F H Cl F A-256 F H Br F A-257Cl H Cl F A-258 Cl Cl Cl F A-259 Cl F Cl F A-260 Cl Br Cl F A-261 Cl HBr F A-262 Br H Br F A-263 Br F Br F A-264 Br Cl Br F A-265 CF₃ H F FA-266 CF₃ H Cl F A-267 CF₃ H Br F A-268 CF₃ H CF₃ F A-269 CF₃ F F FA-270 CF₃ Cl Cl F A-271 CF₃ Br Br F A-272 SF₅ H F F A-273 SF₅ H Cl FA-274 SF₅ H Br F A-275 SF₅ H CF₃ F A-276 F H F Cl A-277 F F F Cl A-278 FCl F Cl A-279 F Br F Cl A-280 F H Cl Cl A-281 F H Br Cl A-282 Cl H Cl ClA-283 Cl Cl Cl Cl A-284 Cl F Cl Cl A-285 Cl Br Cl Cl A-286 Cl H Br ClA-287 Br H Br Cl A-288 Br F Br Cl A-289 Br Cl Br Cl A-290 CF₃ H F ClA-291 CF₃ H Cl Cl A-292 CF₃ H Br Cl A-293 CF₃ H CF₃ Cl A-294 CF₃ F F ClA-295 CF₃ Cl Cl Cl A-296 CF₃ Br Br Cl A-297 SF₅ H F Cl A-298 SF₅ H Cl ClA-299 SF₅ H Br Cl A-300 SF₅ H CF₃ Cl A-301 F H F Br A-302 F F F Br A-303F Cl F Br A-304 F Br F Br A-305 F H Cl Br A-306 F H Br Br A-307 Cl H ClBr A-308 Cl Cl Cl Br A-309 Cl F Cl Br A-310 Cl Br Cl Br A-311 Cl H Br BrA-312 Br H Br Br A-313 Br F Br Br A-314 Br Cl Br Br A-315 CF₃ H F BrA-316 CF₃ H Cl Br A-317 CF₃ H Br Br A-318 CF₃ H CF₃ Br A-319 CF₃ F F BrA-320 CF₃ Cl Cl Br A-321 CF₃ Br Br Br A-322 SF₅ H F Br A-323 SF₅ H Cl BrA-324 SF₅ H Br Br A-325 SF₅ H CF₃ Br A-326 F H F CN A-327 F F F CN A-328F Cl F CN A-329 F Br F CN A-330 F H Cl CN A-331 F H Br CN A-332 Cl H ClCN A-333 Cl Cl Cl CN A-334 Cl F Cl CN A-335 Cl Br Cl CN A-336 Cl H Br CNA-337 Br H Br CN A-338 Br F Br CN A-339 Br Cl Br CN A-340 CF₃ H F CNA-341 CF₃ H Cl CN A-342 CF₃ H Br CN A-343 CF₃ H CF₃ CN A-344 CF₃ F F CNA-345 CF₃ Cl Cl CN A-346 CF₃ Br Br CN A-347 SF₅ H F CN A-348 SF₅ H Cl CNA-349 SF₅ H Br CN A-350 SF₅ H CF₃ CN A-351 F H F OCH₃ A-352 F F F OCH₃A-353 F Cl F OCH₃ A-354 F Br F OCH₃ A-355 F H Cl OCH₃ A-356 F H Br OCH₃A-357 Cl H Cl OCH₃ A-358 Cl Cl Cl OCH₃ A-359 Cl F Cl OCH₃ A-360 Cl Br ClOCH₃ A-361 Cl H Br OCH₃ A-362 Br H Br OCH₃ A-363 Br F Br OCH₃ A-364 BrCl Br OCH₃ A-365 CF₃ H F OCH₃ A-366 CF₃ H Cl OCH₃ A-367 CF₃ H Br OCH₃A-368 CF₃ H CF₃ OCH₃ A-369 CF₃ F F OCH₃ A-370 CF₃ Cl Cl OCH₃ A-371 CF₃Br Br OCH₃ A-372 SF₅ H F OCH₃ A-373 SF₅ H Cl OCH₃ A-374 SF₅ H Br OCH₃A-375 SF₅ H CF₃ OCH₃ A-376 F H F OCH₂CH₃ A-377 F F F OCH₂CH₃ A-378 F ClF OCH₂CH₃ A-379 F Br F OCH₂CH₃ A-380 F H Cl OCH₂CH₃ A-381 F H Br OCH₂CH₃A-382 Cl H Cl OCH₂CH₃ A-383 Cl Cl Cl OCH₂CH₃ A-384 Cl F Cl OCH₂CH₃ A-385Cl Br Cl OCH₂CH₃ A-386 Cl H Br OCH₂CH₃ A-387 Br H Br OCH₂CH₃ A-388 Br FBr OCH₂CH₃ A-389 Br Cl Br OCH₂CH₃ A-390 CF₃ H F OCH₂CH₃ A-391 CF₃ H ClOCH₂CH₃ A-392 CF₃ H Br OCH₂CH₃ A-393 CF₃ H CF₃ OCH₂CH₃ A-394 CF₃ F FOCH₂CH₃ A-395 CF₃ Cl Cl OCH₂CH₃ A-396 CF₃ Br Br OCH₂CH₃ A-397 SF₅ H FOCH₂CH₃ A-398 SF₅ H Cl OCH₂CH₃ A-399 SF₅ H Br OCH₂CH₃ A-400 SF₅ H CF₃OCH₂CH₃ A-401 F H F OCH(CH₃)₂ A-402 F F F OCH(CH₃)₂ A-403 F Cl FOCH(CH₃)₂ A-404 F Br F OCH(CH₃)₂ A-405 F H Cl OCH(CH₃)₂ A-406 F H BrOCH(CH₃)₂ A-407 Cl H Cl OCH(CH₃)₂ A-408 Cl Cl Cl OCH(CH₃)₂ A-409 Cl F ClOCH(CH₃)₂ A-410 Cl Br Cl OCH(CH₃)₂ A-411 Cl H Br OCH(CH₃)₂ A-412 Br H BrOCH(CH₃)₂ A-413 Br F Br OCH(CH₃)₂ A-414 Br Cl Br OCH(CH₃)₂ A-415 CF₃ H FOCH(CH₃)₂ A-416 CF₃ H Cl OCH(CH₃)₂ A-417 CF₃ H Br OCH(CH₃)₂ A-418 CF₃ HCF₃ OCH(CH₃)₂ A-419 CF₃ F F OCH(CH₃)₂ A-420 CF₃ Cl Cl OCH(CH₃)₂ A-421CF₃ Br Br OCH(CH₃)₂ A-422 SF₅ H F OCH(CH₃)₂ A-423 SF₅ H Cl OCH(CH₃)₂A-424 SF₅ H Br OCH(CH₃)₂ A-425 SF₅ H CF₃ OCH(CH₃)₂ A-426 F H FOCH₂CH═CH₂ A-427 F F F OCH₂CH═CH₂ A-428 F Cl F OCH₂CH═CH₂ A-429 F Br FOCH₂CH═CH₂ A-430 F H Cl OCH₂CH═CH₂ A-431 F H Br OCH₂CH═CH₂ A-432 Cl H ClOCH₂CH═CH₂ A-433 Cl Cl Cl OCH₂CH═CH₂ A-434 Cl F Cl OCH₂CH═CH₂ A-435 ClBr Cl OCH₂CH═CH₂ A-436 Cl H Br OCH₂CH═CH₂ A-437 Br H Br OCH₂CH═CH₂ A-438Br F Br OCH₂CH═CH₂ A-439 Br Cl Br OCH₂CH═CH₂ A-440 CF₃ H F OCH₂CH═CH₂A-441 CF₃ H Cl OCH₂CH═CH₂ A-442 CF₃ H Br OCH₂CH═CH₂ A-443 CF₃ H CF₃OCH₂CH═CH₂ A-444 CF₃ F F OCH₂CH═CH₂ A-445 CF₃ Cl Cl OCH₂CH═CH₂ A-446 CF₃Br Br OCH₂CH═CH₂ A-447 SF₅ H F OCH₂CH═CH₂ A-448 SF₅ H Cl OCH₂CH═CH₂A-449 SF₅ H Br OCH₂CH═CH₂ A-450 SF₅ H CF₃ OCH₂CH═CH₂ A-451 F H FO—^(c)C₃H₅* A-452 F F F O—^(c)C₃H₅* A-453 F Cl F O—^(c)C₃H₅* A-454 F BrF O—^(c)C₃H₅* A-455 F H Cl O—^(c)C₃H₅* A-456 F H Br O—^(c)C₃H₅* A-457 ClH Cl O—^(c)C₃H₅* A-458 Cl Cl Cl O—^(c)C₃H₅* A-459 Cl F Cl O—^(c)C₃H₅*A-460 Cl Br Cl O—^(c)C₃H₅* A-461 Cl H Br O—^(c)C₃H₅* A-462 Br H BrO—^(c)C₃H₅* A-463 Br F Br O—^(c)C₃H₅* A-464 Br Cl Br O—^(c)C₃H₅* A-465CF₃ H F O—^(c)C₃H₅* A-466 CF₃ H Cl O—^(c)C₃H₅* A-467 CF₃ H BrO—^(c)C₃H₅* A-468 CF₃ H CF₃ O—^(c)C₃H₅* A-469 CF₃ F F O—^(c)C₃H₅* A-470CF₃ Cl Cl O—^(c)C₃H₅* A-471 CF₃ Br Br O—^(c)C₃H₅* A-472 SF₅ H FO—^(c)C₃H₅* A-473 SF₅ H Cl O—^(c)C₃H₅* A-474 SF₅ H Br O—^(c)C₃H₅* A-475SF₅ H CF₃ O—^(c)C₃H₅* A-476 F H F OCHF₂ A-477 F F F OCHF₂ A-478 F Cl FOCHF₂ A-479 F Br F OCHF₂ A-480 F H Cl OCHF₂ A-481 F H Br OCHF₂ A-482 ClH Cl OCHF₂ A-483 Cl Cl Cl OCHF₂ A-484 Cl F Cl OCHF₂ A-485 Cl Br Cl OCHF₂A-486 Cl H Br OCHF₂ A-487 Br H Br OCHF₂ A-488 Br F Br OCHF₂ A-489 Br ClBr OCHF₂ A-490 CF₃ H F OCHF₂ A-491 CF₃ H Cl OCHF₂ A-492 CF₃ H Br OCHF₂A-493 CF₃ H CF₃ OCHF₂ A-494 CF₃ F F OCHF₂ A-495 CF₃ Cl Cl OCHF₂ A-496CF₃ Br Br OCHF₂ A-497 SF₅ H F OCHF₂ A-498 SF₅ H Cl OCHF₂ A-499 SF₅ H BrOCHF₂ A-500 SF₅ H CF₃ OCHF₂ A-501 F H F OCF₃ A-502 F F F OCF₃ A-503 F ClF OCF₃ A-504 F Br F OCF₃ A-505 F H Cl OCF₃ A-506 F H Br OCF₃ A-507 Cl HCl OCF₃ A-508 Cl Cl Cl OCF₃ A-509 Cl F Cl OCF₃ A-510 Cl Br Cl OCF₃ A-511Cl H Br OCF₃ A-512 Br H Br OCF₃ A-513 Br F Br OCF₃ A-514 Br Cl Br OCF₃A-515 CF₃ H F OCF₃ A-516 CF₃ H Cl OCF₃ A-517 CF₃ H Br OCF₃ A-518 CF₃ HCF₃ OCF₃ A-519 CF₃ F F OCF₃ A-520 CF₃ Cl Cl OCF₃ A-521 CF₃ Br Br OCF₃A-522 SF₅ H F OCF₃ A-523 SF₅ H Cl OCF₃ A-524 SF₅ H Br OCF₃ A-525 SF₅ HCF₃ OCF₃ A-526 F H F OCH₂CF₃ A-527 F F F OCH₂CF₃ A-528 F Cl F OCH₂CF₃A-529 F Br F OCH₂CF₃ A-530 F H Cl OCH₂CF₃ A-531 F H Br OCH₂CF₃ A-532 ClH Cl OCH₂CF₃ A-533 Cl Cl Cl OCH₂CF₃ A-534 Cl F Cl OCH₂CF₃ A-535 Cl Br ClOCH₂CF₃ A-536 Cl H Br OCH₂CF₃ A-537 Br H Br OCH₂CF₃ A-538 Br F BrOCH₂CF₃ A-539 Br Cl Br OCH₂CF₃ A-540 CF₃ H F OCH₂CF₃ A-541 CF₃ H ClOCH₂CF₃ A-542 CF₃ H Br OCH₂CF₃ A-543 CF₃ H CF₃ OCH₂CF₃ A-544 CF₃ F FOCH₂CF₃ A-545 CF₃ Cl Cl OCH₂CF₃ A-546 CF₃ Br Br OCH₂CF₃ A-547 SF₅ H FOCH₂CF₃ A-548 SF₅ H Cl OCH₂CF₃ A-549 SF₅ H Br OCH₂CF₃ A-550 SF₅ H CF₃OCH₂CF₃ A-551 F H F SCH₃ A-552 F F F SCH₃ A-553 F Cl F SCH₃ A-554 F Br FSCH₃ A-555 F H Cl SCH₃ A-556 F H Br SCH₃ A-557 Cl H Cl SCH₃ A-558 Cl ClCl SCH₃ A-559 Cl F Cl SCH₃ A-560 Cl Br Cl SCH₃ A-561 Cl H Br SCH₃ A-562Br H Br SCH₃ A-563 Br F Br SCH₃ A-564 Br Cl Br SCH₃ A-565 CF₃ H F SCH₃A-566 CF₃ H Cl SCH₃ A-567 CF₃ H Br SCH₃ A-568 CF₃ H CF₃ SCH₃ A-569 CF₃ FF SCH₃ A-570 CF₃ Cl Cl SCH₃ A-571 CF₃ Br Br SCH₃ A-572 SF₅ H F SCH₃A-573 SF₅ H Cl SCH₃ A-574 SF₅ H Br SCH₃ A-575 SF₅ H CF₃ SCH₃ A-576 F H FSCH₂CH₃ A-577 F F F SCH₂CH₃ A-578 F Cl F SCH₂CH₃ A-579 F Br F SCH₂CH₃A-580 F H Cl SCH₂CH₃ A-581 F H Br SCH₂CH₃ A-582 Cl H Cl SCH₂CH₃ A-583 ClCl Cl SCH₂CH₃ A-584 Cl F Cl SCH₂CH₃ A-585 Cl Br Cl SCH₂CH₃ A-586 Cl H BrSCH₂CH₃ A-587 Br H Br SCH₂CH₃ A-588 Br F Br SCH₂CH₃ A-589 Br Cl BrSCH₂CH₃ A-590 CF₃ H F SCH₂CH₃ A-591 CF₃ H Cl SCH₂CH₃ A-592 CF₃ H BrSCH₂CH₃ A-593 CF₃ H CF₃ SCH₂CH₃ A-594 CF₃ F F SCH₂CH₃ A-595 CF₃ Cl ClSCH₂CH₃ A-596 CF₃ Br Br SCH₂CH₃ A-597 SF₅ H F SCH₂CH₃ A-598 SF₅ H ClSCH₂CH₃ A-599 SF₅ H Br SCH₂CH₃ A-600 SF₅ H CF₃ SCH₂CH₃ A-601 F H FSCH(CH₃)₂ A-602 F F F SCH(CH₃)₂ A-603 F Cl F SCH(CH₃)₂ A-604 F Br FSCH(CH₃)₂ A-605 F H Cl SCH(CH₃)₂ A-606 F H Br SCH(CH₃)₂ A-607 Cl H ClSCH(CH₃)₂ A-608 Cl Cl Cl SCH(CH₃)₂ A-609 Cl F Cl SCH(CH₃)₂ A-610 Cl BrCl SCH(CH₃)₂ A-611 Cl H Br SCH(CH₃)₂ A-612 Br H Br SCH(CH₃)₂ A-613 Br FBr SCH(CH₃)₂ A-614 Br Cl Br SCH(CH₃)₂ A-615 CF₃ H F SCH(CH₃)₂ A-616 CF₃H Cl SCH(CH₃)₂ A-617 CF₃ H Br SCH(CH₃)₂ A-618 CF₃ H CF₃ SCH(CH₃)₂ A-619CF₃ F F SCH(CH₃)₂ A-620 CF₃ Cl Cl SCH(CH₃)₂ A-621 CF₃ Br Br SCH(CH₃)₂A-622 SF₅ H F SCH(CH₃)₂ A-623 SF₅ H Cl SCH(CH₃)₂ A-624 SF₅ H BrSCH(CH₃)₂ A-625 SF₅ H CF₃ SCH(CH₃)₂ A-626 F H F SCH₂CH═CH₂ A-627 F F FSCH₂CH═CH₂ A-628 F Cl F SCH₂CH═CH₂ A-629 F Br F SCH₂CH═CH₂ A-630 F H ClSCH₂CH═CH₂ A-631 F H Br SCH₂CH═CH₂ A-632 Cl H Cl SCH₂CH═CH₂ A-633 Cl ClCl SCH₂CH═CH₂ A-634 Cl F Cl SCH₂CH═CH₂ A-635 Cl Br Cl SCH₂CH═CH₂ A-636Cl H Br SCH₂CH═CH₂ A-637 Br H Br SCH₂CH═CH₂ A-638 Br F Br SCH₂CH═CH₂A-639 Br Cl Br SCH₂CH═CH₂ A-640 CF₃ H F SCH₂CH═CH₂ A-641 CF₃ H ClSCH₂CH═CH₂ A-642 CF₃ H Br SCH₂CH═CH₂ A-643 CF₃ H CF₃ SCH₂CH═CH₂ A-644CF₃ F F SCH₂CH═CH₂ A-645 CF₃ Cl Cl SCH₂CH═CH₂ A-646 CF₃ Br Br SCH₂CH═CH₂A-647 SF₅ H F SCH₂CH═CH₂ A-648 SF₅ H Cl SCH₂CH═CH₂ A-649 SF₅ H BrSCH₂CH═CH₂ A-650 SF₅ H CF₃ SCH₂CH═CH₂ A-651 F H F S—^(c)C₃H₅* A-652 F FF S—^(c)C₃H₅* A-653 F Cl F S—^(c)C₃H₅* A-654 F Br F S—^(c)C₃H₅* A-655 FH Cl S—^(c)C₃H₅* A-656 F H Br S—^(c)C₃H₅* A-657 Cl H Cl S—^(c)C₃H₅*A-658 Cl Cl Cl S—^(c)C₃H₅* A-659 Cl F Cl S—^(c)C₃H₅* A-660 Cl Br ClS—^(c)C₃H₅* A-661 Cl H Br S—^(c)C₃H₅* A-662 Br H Br S—^(c)C₃H₅* A-663 BrF Br S—^(c)C₃H₅* A-664 Br Cl Br S—^(c)C₃H₅* A-665 CF₃ H F S—^(c)C₃H₅*A-666 CF₃ H Cl S—^(c)C₃H₅* A-667 CF₃ H Br S—^(c)C₃H₅* A-668 CF₃ H CF₃S—^(c)C₃H₅* A-669 CF₃ F F S—^(c)C₃H₅* A-670 CF₃ Cl Cl S—^(c)C₃H₅* A-671CF₃ Br Br S—^(c)C₃H₅* A-672 SF₅ H F S—^(c)C₃H₅* A-673 SF₅ H ClS—^(c)C₃H₅* A-674 SF₅ H Br S—^(c)C₃H₅* A-675 SF₅ H CF₃ S—^(c)C₃H₅* A-676F H F SCF₃ A-677 F F F SCF₃ A-678 F Cl F SCF₃ A-679 F Br F SCF₃ A-680 FH Cl SCF₃ A-681 F H Br SCF₃ A-682 Cl H Cl SCF₃ A-683 Cl Cl Cl SCF₃ A-684Cl F Cl SCF₃ A-685 Cl Br Cl SCF₃ A-686 Cl H Br SCF₃ A-687 Br H Br SCF₃A-688 Br F Br SCF₃ A-689 Br Cl Br SCF₃ A-690 CF₃ H F SCF₃ A-691 CF₃ H ClSCF₃ A-692 CF₃ H Br SCF₃ A-693 CF₃ H CF₃ SCF₃ A-694 CF₃ F F SCF₃ A-695CF₃ Cl Cl SCF₃ A-696 CF₃ Br Br SCF₃ A-697 SF₅ H F SCF₃ A-698 SF₅ H ClSCF₃ A-699 SF₅ H Br SCF₃ A-700 SF₅ H CF₃ SCF₃ A-701 F H F SCH₂CF₃ A-702F F F SCH₂CF₃ A-703 F Cl F SCH₂CF₃ A-704 F Br F SCH₂CF₃ A-705 F H ClSCH₂CF₃ A-706 F H Br SCH₂CF₃ A-707 Cl H Cl SCH₂CF₃ A-708 Cl Cl ClSCH₂CF₃ A-709 Cl F Cl SCH₂CF₃ A-710 Cl Br Cl SCH₂CF₃ A-711 Cl H BrSCH₂CF₃ A-712 Br H Br SCH₂CF₃ A-713 Br F Br SCH₂CF₃ A-714 Br Cl BrSCH₂CF₃ A-715 CF₃ H F SCH₂CF₃ A-716 CF₃ H Cl SCH₂CF₃ A-717 CF₃ H BrSCH₂CF₃ A-718 CF₃ H CF₃ SCH₂CF₃ A-719 CF₃ F F SCH₂CF₃ A-720 CF₃ Cl ClSCH₂CF₃ A-721 CF₃ Br Br SCH₂CF₃ A-722 SF₅ H F SCH₂CF₃ A-723 SF₅ H ClSCH₂CF₃ A-724 SF₅ H Br SCH₂CF₃ A-725 SF₅ H CF₃ SCH₂CF₃ *^(c)C₃H₅ ═cyclopropyl

Among the above compounds, preference is given to compounds Ia.1, Ia.13,Ia.17, Ia.19 and Ia.20 and especially to Ia.13.

The compounds of the formula (I) can be prepared by novel methods asdescribed below or and in the synthesis descriptions of the workingexamples, or by standard methods of organic chemistry, e.g. by themethods described hereinafter or in the synthesis descriptions of theworking examples. The substituents, variables and indices are as definedabove for formula (I), if not otherwise specified.

The invention relates to a method for preparing compounds of formula Ias defined in any of the preceding claims, where however R^(3b) ishydrogen, which method comprises dehydrating a compound of formula II

wherein B¹, B², B³, G¹, G², G³, G⁴, R¹, R^(3a) and R^(3b) are as definedabove and A′ is A or a precursor of A;to give a compound I′

and, if necessary (i.e. if A′ is a precursor of A), converting the groupA′ into a group A.

A′ as a precursor of A is typically a halogen atom, CN, carboxy,tert-butoxycarbonyl, an acetale group, a protected aldehyde group or—OSO₂—R^(z1), where R^(z1) is C₁-C₄-alkyl, C₁-C₄-haloalkyl or phenylwhich may be substituted by 1, 2 or 3 radicals selected fromC₁-C₄-alkyl, C₁-C₄-haloalkyl C₁-C₄-alkoxy or C₁-C₄-haloalkoxy. A′ as aprecursor of A is preferably a halogen atom or —OSO₂—R^(z1), whereR^(z1) is as defined above, and is more preferably a halogen atom orOtriflate.

Dehydration either occurs spontaneously or with the help of dehydratingagents, such as molecular sieves, acid-washed molecular sieves,magnesium sulfate, sodium sulfate, silica gel, SOCl₂, POCl₃, Burgessreagent, trifluoroacetic anhydride, p-toluene sulfonic acid, anhydrousHCl or sulfuric acid. Preferably, p-toluene sulfonic acid or acid-washedmolecular sieves are used. The water formed may alternatively beremoved, e.g. by azeotropic distillation, e.g. with benzene/toluene asentrainer, e.g. using a Dean Stark trap.

The compound of formula II, in which R^(3b) is hydrogen, is preferablyobtained by reacting a compound of formula IV

with an amination agent to give a compound of formula I with anamination agent to give a compound of formula III

which reacts spontaneously to the compound II;wherein B¹, B², B³, G¹, G², G³, G⁴, R¹ and R^(3a) are as defined aboveand A′ is A or a precursor of A.

Depending on the amination agents used, amination can the carried out ina one step reaction, wherein compound IV reacts directly to compoundIII, or as a two step reaction, wherein the SH group of compound IV isfirst oxidized to a S—Cl group, which then further reacts to a S—NH₂group, thus giving compound III.

Suitable amination agents for the one step reaction are for example HOSA(hydroxylamine-O-sulfonic acid), which is generally used in the presenceof a base (suitable bases being for example sodium hydrogen phosphate,potassium hydrogen phosphate, sodium hydroxide, potassium hydroxide,sodium carbonate, potassium carbonate, sodium methanolate, triethylamineand the like), O-(diphenylphosphoryl)hydroxylamine, which is generallyalso used in the presence of a base (suitable bases being for examplesodium hydrogen phosphate, potassium hydrogen phosphate, sodiumhydroxide, potassium hydroxide, sodium carbonate, potassium carbonate,sodium methanolate, triethylamine and the like),2,4-dinitrophenylhydroxyl amine, O-mesitylensulfonylhydroxylamine and2-oxa-1-azaspiro[2.5]octane, among which HOSA andO-(diphenylphosphoryl)hydroxylamine are preferred.

The amination is preferably carried out in a solvent, suitable solventsbeing for example chlorinated alkanes, such as methylene chloride orchloroform, aromatic solvents, such as benzene, toluene, the xylenes,chlorobenzene or dichlorobenzene, and ethers, such as diethylether,dipropylether, methyl tert-butylether, methyl isobutylether,ethylenegylcol dimethylether, tetrahydrofuran (THF) or dioxane and thelike.

The reaction is suitably carried out low temperature, e.g. at from −100to 0° C. or −78 to 0° C.

Generally, the compound IV is dispersed in a solvent and cooled to thedesired temperature and the base is added followed by the aminationagent, or the amination agent is added followed by the base, or base andamination agent are added simultaneously.

In a preferred embodiment, HOSA is used in combination with an aminebase, such as triethylamine. In this case, it is preferred to coolcompound IV to −30 to 0° C., preferably −20 to −10° C., to add the aminebase at this temperature and then HOSA and keep the reaction atapproximately −10 to 0° C.

In an alternatively preferred embodiment,O-(diphenylphosphoryl)hydroxylamine is used in combination with a base,preferably with an inorganic base, such as sodium hydrogen phosphate,potassium hydrogen phosphate, sodium hydroxide, potassium hydroxide,sodium carbonate or potassium carbonate and specifically sodium hydrogenphosphate. In this case, it is preferred to cool compound IV to −80 to−30° C., preferably −80 to −70° C., to add the base at this temperatureand then O-(diphenylphosphoryl)hydroxylamine and keep the reaction atapproximately 0° C. to room temperature.

In the two step reaction, the compound IV is first reacted with achlorination agent which converts the SH group into an S—Cl group.Suitable chlorination agents are for example sulfurylchloride, N-chlorosuccinimide (NCS), sodium hypochlorite, monochloroamine (NH₂Cl) orchlorine, which is preferably used in the presence of FeCl₃. Thechlorination can be carried out in analogy to the method described inSynthesis 1987, 1987, 683-688, Tetrahedron 66(36), 2010, 7279-7287, J.Org. Chem. 59(4), 1994, 914-921, J. Org. Chem. 63, 1998, 4878-4888 or J.Chem. Soc. 1938, 2114-2117.

The chlorination is generally carried out in a solvent. Suitablesolvents are for example ethers, such as diethylether, dipropylether,methyl tert-butylether, methyl isobutylether, ethylenegylcoldimethylether, tetrahydrofuran or dioxane.

The reaction temperature can vary over wide ranges and is generally from0° C. to the boiling point of the reaction mixture (if a solvent isused).

The chlorinated compound is then reacted without isolation with ammoniaor ammonium hydroxide.

If anhydrous ammonia is used, the reaction is generally carried out atfrom −78 to −33° C. If aqueous ammonia or ammonium hydroxide is used,the reaction can also be carried out at higher temperatures, such as 0to 25° C.

The reaction is generally carried out in a solvent. Suitable solventsare for example the above-listed ethers, among which the water-miscibleethers, such as THF and dioxane, are preferred. In general, thechlorinated compound is dissolved in a solvent to which ammonia orammonium hydroxide is added. The reaction can be carried out asdescribed, for example, in Synthesis, 1987, 8, 683-688.

The chlorination/amination can also be carried as a one pot reaction.For example, the thiol IV is reacted simultaneously with a chlorinatingagent (such as NCS or aqueous sodium hypochlorite) and anhydrous oraqueous ammonia in ethereal solvents (such as THF or Et₂O) or water.Preferred is the reaction with NCS in a mixture of THF and anhydrousliquid ammonia at −33° C. For instance, a solution of the thiol IV inTHF is added to a solution of NCS(N-chlorosuccinimide) in THF/liquidammonia at −78° C. The solution is warmed to −30° C. and stirred untilthe ammonia has evaporated. Alternatively, at 0° C., a solution of thesodium thiolate (NaSR) in water is added to a mixture of aqueous ammonia(25%) and aqueous sodium hypochlorite (1 N). The one potchlorination/amination reaction can be carried out as described, forexample, in Tetrahedron 2010, 66, 7279-7287 or in J. Org. Chem. 1994,59, 914-921.

Compound III can virtually not be isolated as it generally reactsspontaneously in a ring-closing reaction to compound II.

The compound of formula IV is preferably prepared by reacting a compoundof formula V

wherein B¹, B², B³, G¹, G², G³, G⁴, R¹ and R^(3a) are as defined in anyof claims 1 to 32 and A′ is A or a precursor of A;with a sulfur source.

Suitable sulfur sources are for example H₂S, metal hydrogen sulfides,such as NaSH or KSH, metal sulfides, such as Na₂S, K₂S Li₂S, Cu₂S, MgS,CaS, CuS, FeS and the like, ammonium sulfide [(NH₄)₂S],tetraalkylammonium sulfides (R₄NSH), such as tetramethylammoniumsulfide, tetraethylammonium sulfide, tetrapropylammonium sulfide and thelike, or bistrimethylsilyl sulfide.

H₂S as a sulfur source is generally used in the presence of a base, suchas Na₂CO₃, K₂CO₃, Cs₂CO₃, sodium acetate, potassium acetate, cesiumacetate, amines, such as diethylamine, dipropylamine, triethylamine,diisopropylethylamine and the like, or basic nitrogen-containingheterocycles, such as pyrrolidine, piperidine, piperazine, pyridine,lutidine and the like.

Alternatively, H₂S as a sulfur source can be used in the presence of aLewis acid, such as AlCl₃ or FeCl₃.

The reaction of compound V with a sulfur source is generally carried outin a solvent, suitable solvents being for example chlorinated alkanes,such as methylene chloride or chloroform, and aromatic solvents, such asbenzene, toluene, the xylenes, chlorobenzene or dichlorobenzene.

The reaction temperature can vary over a wide range, such as −78° C. toroom temperature.

In general, compound V is dissolved in a solvent, optionally cooled,then the base (if used) and subsequently the sulfur source is added

The compound V can alternatively be reacted with a sulfur source whichprovides a compound IV which is protected at the thiol group SH by aprotective group (S-PG).

This is advantageous if compound IV is for example subjected to harsherpurification conditions or is derivatized, e.g. for converting theprecursor group A′ into a group A or for modifying group A′ at thisstage. Moreover, purification of the protected product is easier.

Suitable sulfuration reagents which give such protected thiols are forexample thiourea (NH₂—C(═S)—NH₂), optionally substituted benzyl thiols,such as benzylthiol, o- or p-methoxy-benzylthiol, o- orp-hydroxybenzylthiol, o- or p-acetoxybenzylthiol, o- orp-nitrobenzylthiol or 2,4,6-trimethylbenzylthiol,pyridin-4-yl-methylthiol, quinolin-2-yl-methylthiol, benzyl metalsulfides, such as sodium benzylsulfide, phenylthiol,2,4-dinitrophenylthiol, tritylthiol, tert-butylthiol, compounds offormula R—C(═O)—NH—CH₃—SH, wherein R is methyl, tert-butyl, allyl,phenyl or benzyl, 2-trimethylsilanyl-ethanethiol,2-(2,4-dinitrophenyl)-ethanethiol, 2-phenylsulfonyl-ethanethiol,acylated thiols, such as methylcarbonylthiol or phenylcarbonylthiol, andthiocarbamates R—NH—C(═O)—SH, wherein R is e.g. methyl or ethyl.

The benzyl and alkyl thiols are generally used in the presence of abase, such as sodium hydroxide, potassium hydroxide, sodium phosphate,potassium phosphate, sodium hydrogenphosphate, potassiumhydrogenphosphate, sodium carbonate, potassium carbonate, caesiumcarbonate, sodium hydride, potassium hydride, lithium diisopropyl amide(LDA), sodium methanolate, sodium ethanolate, potassium tert-butoxide,aqueous sodium tetraborate, n-butyllithium, tert-butylithium,tetrabutylammoniumfluoride (TBAF), NaHMDS and the like, or in thepresence of a Lewis or Bronsted acid, such as FeCl₃, Zn(ClO₄)₂,Cu(BF₄)₂, HBF₄ or HClO₄.

The reaction is preferably carried out in a solvent, suitable solventsbeing for example chlorinated alkanes, such as methylene chloride orchloroform, and ethers, such as diethylether, dipropylether, methyltert-butylether, methyl isobutylether, ethylenegylcol dimethylether,tetrahydrofuran (THF) or dioxane and the like.

The reaction temperature can vary over a wide range, such as from −25°C. to the boiling point of the reaction mixture.

The acylated thiols can be reacted neat or in a solvent, suitablesolvents being for example chlorinated alkanes, such as methylenechloride or chloroform, and ethers, such as diethylether, dipropylether,methyl tert-butylether, methyl isobutylether, ethylenegylcoldimethylether, tetrahydrofuran (THF) or dioxane and the like. They canbe used with or without a base.

The S-protected compound IV can then be deprotected to the free thiol IVunder conditions generally known for the respective protective group,such as described, for example, in Peter G. M. Wuts, Theodora Greene,Protective Groups in Organic Synthesis, 4^(th) edition, John Wiley &Sons, Inc., 2007, Chapter 6.

Among the above sulfur sources, preference is given to H₂S, especiallyused in the presence of a base, such as Na₂CO₃, K₂CO₃, Cs₂CO₃, sodiumacetate, potassium acetate, cesium acetate, amines, such asdiethylamine, dipropylamine, triethylamine, diisopropylethylamine andthe like, or basic nitrogen-containing heterocycles, such aspyrrolidine, piperidine, piperazine, pyridine, lutidine and the like,and preferably in the presence of an amine, such as triethylamine.

In a preferred embodiment of the method of the invention, the reactionof compound IV to compound I′ via compounds III and II is carried out asa one-pot reaction.

In an alternatively preferred embodiment of the method of the invention,the reaction of compound V to compound I′ via compounds IV, III and IIis carried out as a one-pot reaction.

Compound V can be prepared in analogy to the method described inEP-A-2172462.

Compounds II (in which R^(3b) is not necessarily hydrogen) can beprepared alternatively by reacting a compound of formula VII

with an amination agent to give a compound of formula VI

which reacts spontaneously to the compound II;wherein B¹, B², B³, G¹, G², G³, G⁴, R¹, R^(3a) and R^(3b) are as definedabove and A′ is A or a precursor of A.

The reaction can be carried out in analogy to that of compounds IV andIII.

The compound of formula VII is preferably obtained by reacting acompound of formula VIII with a compound of formula IX

The reaction is preferably carried out as a Mukaiyama aldol reaction. Tothis purpose, the trialklysilyl-enolate derivative of IX is reacted withVIII in the presence of a Lewis acid, such as TiCl₄ or BF₃[O(C₂H₅)₂].Alternatively, the reaction can be carried out in the presence of astrong base, such as lithium diisopropylamide (LDA), sodiumbistrimethylsilylamide (sodium hexamethyldisilazide; NaHMDS) and amines,such as triethylamine, tripropylamine or diisopropylethylamine.

The reaction is generally carried out in a solvent.

If a lithium or sodium base is used, the solvent is suitably an ether,such as diethylether, dipropylether, methyl tert-butylether, methylisobutylether, ethylenegylcol dimethylether, tetrahydrofuran (THF) ordioxane and the like. Suitable reaction temperatures range from −78 to25° C.

If an amine base is used, the solvent is suitably an ether, such asdiethylether, dipropylether, methyl tert-butylether, methylisobutylether, ethylenegylcol dimethylether, tetrahydrofuran (THF) ordioxane, or an alkane, such as pentane, hexane or heptane. Suitablereaction temperatures range from 25 to 100° C.

The compound of formula VIII can be obtained by reacting a compound offormula X with a sulfuration agent, such as Lawesson's reagent or P₂S₅

The reaction is generally carried out in a solvent, suitable solventsbeing for example aromatic solvents, such as benzene, toluene, thexylenes, chlorobenzene or dichlorobenzene, ethers, such as diethylether,dipropylether, methyl tert-butylether, methyl isobutylether,ethylenegylcol dimethylether, tetrahydrofuran (THF) or dioxane, andhexamethyl phosphoric acid triamide (HMPA).

The reaction is generally carried out at a temperature of from 25° C. tothe boiling point of the reaction mixture.

The invention further relates to a method for preparing compounds offormula I as defined above, wherein R¹ is CF₃, which method comprisesreacting a compound of formula XI

wherein B¹, B², B³, G¹, G², G³, G⁴, R^(3a) and R^(3b) are as definedabove and A′ is A or a precursor of A;with a fluorinating agentto give a compound I″

and, if necessary (i.e. if A′ is a precursor of A), converting the groupA′ into a group A.

Suitable fluorinating agents are, for example, SF₄, preferably incombination with HF or BF₃[O(C₂H₅)₂], phenylsulfur trifluoride (Ph-SF₃),preferably in combination with HF and pyridine,4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (“Fluoled”), andbis(2-methoxyethyl)aminosulfur trifluoride [(CH₃OCH₂CH₂)₂NSF₃]. Amongthese, preference is given to SF₄ in combination with HF.

If SF₄ in combination with HF is used, the reaction is carried out neat,i.e. without any further solvent. The reaction is generally carried outunder elevated pressure stemming from the reactants, e.g. at a pressureof from 2 to 10 bar, preferably from 5 to 8 bar. The reactiontemperature can vary over wide ranges, such as from 25 to 120° C.,preferably from 60 to 100° C.

Alternatively, fluorination can be carried out by a two step method, inwhich the carboxyl group on the isothiazoline ring is first convertedinto a CCl₃ group, and this is subsequently fluorinated to the CF₃group.

The conversion of the COOH group to the CCl₃ group is preferably carriedout by reacting the compound VI with PCl₅ and phenyl-phosphoroxydichloride (Ph-P(═O)Cl₂).

The reaction can be carried out neat, i.e. without any further solvent.Suitably, the reaction is carried out at elevated temperatures, forexample at from 50° to reflux and preferably at reflux.

Fluorination agents for converting the CCl₃ group into a CF3 group arethose mentioned above, and further HF and HF in combination with SbCl₅and HF in combination with Cl₂ and SbF₃.

The reaction can be carried out neat, i.e. without any further solvent.The reaction temperature can vary over wide ranges, for examples from 25to 300° C., preferably from 50 to 200° C. and in particular from 80 to120° C. If the fluorination agent is HF or HF in combination with afurther agent, the reaction generally takes place at the pressurestemming from HF and ranging generally from 2 to 10 bar, preferably from5 to 8 bar.

The compound of formula XI is preferably obtained by hydrolyzing acompound of formula XII

wherein B¹, B², B³, G¹, G², G³, G⁴, R^(3a) and R^(3b) are as definedabove, A′ is A or a precursor of A and R is C₁-C₄-alkyl.

Hydrolysis can be carried out by any suitable means known forhydrolyzing ester groups, such as acidic conditions, e.g. usinghydrochloric acid, hydrobromic acid, sulfuric acid, trifluoroaceticacid, etc., or by basic conditions, e.g. using an alkali metalhydroxide, such as LiOH, NaOH or KOH, or an alkali metal carbonate, suchas sodium or potassium carbonate.

The compound of formula XII is in turn preferably obtained by reacting acompound XIII with a compound XIV

wherein B¹, B², B³, G¹, G², G³, G⁴, R¹, R^(3a) and R^(3b) are as definedabove, A′ is A or a precursor of A and R is C₁-C₄-alkyl.

The reaction is carried out at elevated temperature, e.g. at from 90 to200° C., preferably from 100 to 180° C. and in particular from 120 to160° C., e.g. at about 140° C.

The compound of formula XIII can in turn be obtained by reacting acompound XVI with a compound XVII

The reaction is generally carried out in a solvent, suitable solventsbeing for example aromatic solvents, such as benzene, toluene, thexylenes, chlorobenzene and dichlorobenzene. The reaction temperature ispreferably from 80 to 140° C., more preferably from 100 to 120° C.

The invention further relates to a method for preparing compounds offormula I as defined above, wherein however R¹ is CF₃, which methodcomprises reacting a compound of formula XIII as defined above with acompound of formula XV

wherein B¹, B², B³, R^(3a) and R^(3b) are as defined above,to give a compound I″

and, if necessary, converting the group A′ into a group A.

The reaction is carried out at elevated temperature, e.g. at from 90 to200° C., preferably from 100 to 180° C. and in particular from 120 to160° C., e.g. at about 140° C.

Compounds I′ or I″, in which A′ is a precursor of A can be converted asshown below into the different groups A¹ to A⁴.

Compounds I′ or I″, in which A′ is Cl, Br, I or —OSO₂—R^(z1), whereR^(z1) is as defined above, can be converted to compounds I wherein A isa group A¹, wherein A is an imino group —C(═NR⁶)R⁸, by reaction withcarbon monoxide and a hydride source, such as triethylsilane, in thepresence of a transition metal complex catalyst, preferably a palladiumcatalyst, to a carbonyl compound XVIII. This reaction converts thestarting group A′ into a carbonyl group —C(═O)H.

The aldehyde XVIII can also be obtained by reducing the methyl ester XXI(see below; R=methyl) with diisobutylaluminium hydride (DIBAL-H) eitherdirectly to the aldehyde XVIII or via the corresponding alcohol, whichis then oxidized to the aldehyde.

For obtaining compounds in which R⁸ in the imino group is H, suchcarbonyl compounds XVIII are then reacted with an amine (derivative)NH₂R⁶. Alternatively, the compound I′ or I″, in which A′ is Cl, Br, I or—OSO₂—R^(z1), where R^(z1) is as defined above, can be reacted in a onepot reaction with carbon monoxide and hydrogen in the presence of atransition metal complex catalyst and the amine NH₂R⁶.

For obtaining compounds in which R⁸ in the imino group is not H, thecarbonyl compounds are reacted with a Grignard reagent R⁸—MgHal, whereHal is Cl, Br or I, or an organolithium compound R⁸—Li to obtain analcohol of formula XIX

which is then oxidized to a carbonyl compound of the formula XX

This is then reacted with an amine NH₂R⁶ to the respective iminecompound.

These reactions can be carried out in analogy to the methods describedin PCT/EP 2011/060388 or in WO 2010/072781 and the references citedtherein, especially WO 2006135763, Fattorusso et al, J. Med. Chem. 2008,51, 1333-1343 and WO 2008/122375.

Compounds I wherein A is a group A¹, wherein A¹ is —S(O)_(n)R⁹ or—N(R⁵)R⁶, can for example be prepared by reacting a compound I′ or I″wherein A′ is Cl, Br or I in a Ullmann-type reaction with an amineNHR⁵R⁶ or a thiol SHR⁹ in the presence of a Cu(I) catalyst. To obtain acompound wherein A is —S(O)_(n)R⁹ wherein n is not 0 the thiol can thenbe oxidized, e.g. with hydrogen peroxide. Amine and thiol groups canfurther be introduced in a Buchwald-Hartwig reaction by reacting acompound I′ or I″ wherein A′ is Cl, Br or I with an amine NHR⁵R⁶ or athiol HSR⁹ in the presence of a palladium catalyst, such as PdCl₂(dppf)in the presence of a base, such as cesium carbonate orN,N-diisopropylethyl amine, and optionally in the presence of aphosphine ligand, such as Xantphos(“4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene”).

Thioethers (A¹=—SR⁹) can further be introduced by reacting a compound I′or I″ wherein A′ is F in an S_(N)Ar reaction (nucleophilic aromaticsubstitution reaction) with a thiol HSR⁹ in the presence of a base, suchas potassium carbonate (K₂CO₃), or with a thiolate (e.g. NaSR⁹).

Compounds I wherein A is a group A², wherein W is O and Y is OR⁹ can beprepared by reacting a compound I′ or I″ wherein A′ is Cl, Br, I orOtriflate with carbon monoxide in the presence of a palladium catalystand an alcohol R⁹OH. Compounds I wherein A is a group A², wherein W is Oand Y is NR⁵R⁶ can be prepared by reacting a compound I′ or I″ whereinA′ is Cl, Br, I or Otriflate with carbon monoxide in the presence of apalladium catalyst and an alcohol ROH, wherein R is C₁-C₄-alkyl, to acompound of formula XXI. Suitable palladium catalysts are for examplethose described in PCT/EP 2011/060388.

This ester is then hydrolyzed to the respective carboxylic acid, whichis the reacted under standard amidation conditions with an amine NHR⁵R⁶.Hydrolyzation can be carried out under standard conditions, e.g. underacidic conditions using for example hydrochloric acid, sulfuric acid ortrifluoroacetic acid, or under basic conditions using for example analkali metal hydroxide, such as LiOH, NaOH or KOH. Amidation ispreferably carried out by activation of the carboxylic acids withoxalylchloride [(COCl)₂] or thionylchloride (SOCl₂) to the respectiveacid chlorides, followed by reaction with an amine NHR⁵R⁶.Alternatively, amidation is carried out in in the presence of a couplingreagent. Suitable coupling reagent (activators) are well known and arefor instance selected from carbodiimides, such as DCC(dicyclohexylcarbodiimide) and DCI (diisopropylcarbodiimide),benzotriazol derivatives, such as HATU(O-(7-azabenzotriazol-1-yl)N,N,N′,N′-tetramethyluroniumhexafluorophosphate), HBTU(1H-benzotriazol-1-yl)N,N,N′,N′-tetramethyluronium hexafluorophosphate)and HCTU (1H-benzotriazolium-1-[bis(dimethylamino)methylene]-5-chlorotetrafluoroborate) and phosphonium-derived activators, such as BOP((benzotriazol-1-yloxy)-tris(dimethylamino)phosphoniumhexafluorophosphate), Py-BOP((benzotriazol-1-yloxy)-tripyrrolidinphosphonium hexafluorophosphate)and Py-BrOP (bromotripyrrolidinphosphonium hexafluorophosphate).Generally, the activator is used in excess. The benzotriazol andphosphonium coupling reagents are generally used in a basic medium.

Compounds I wherein A is a group A², wherein W is S and Y is NR⁵R⁶ orOR⁹, can be prepared by reacting the corresponding oxo-compound (W is O)with Lawesson's reagent (CAS19172-47-5), see for example Jesberger etal., Synthesis, 2003, 1929-1958 and references therein. For compoundswherein Y is NR⁵R⁶, solvents such as HMPA or THF at an elevatedtemperature such as 60° C. to 100° C. can be used. Preferred reactionconditions are THF at 65° C. For compounds wherein Y is OR⁹, solventfree conditions or solvents such as toluene at temperatures such as 100°C. to 200° C., preferably 140° C., are suitable reaction conditions.

Compounds I wherein A is a group A³, wherein R^(7a) and R^(7b) arehydrogen, can be prepared by reducing a compound XXI or XVIII forexample with LAH (lithium aluminium hydride) or DIBAL-H (diisobutylaluminium hydride) to a compound XXII.

This is then reacted in an S_(N) reaction with an amine NHR⁵R⁶. For thispurpose, the OH group can first be converted into a better leavinggroup, e.g. into a sulfonate (for example mesylate, tosylate or atriflate group). If R⁶ is a group —C(O)R⁸, it is alternatively possibleto react compound XXII with an amine NH₂R⁵ and react then the resultingbenzylic amine with an acid R⁸—COOH or a derivative thereof, such as itsacid chloride R⁸—COCl, in an amidation reaction.

Compounds I wherein A is a group A³, wherein R^(7a) is optionallysubstituted alkyl or optionally substituted cycloalkyl and R^(7b) ishydrogen, can be prepared by subjecting a ketone XX, in which R⁸corresponds to R^(7a) which is optionally substituted C₁-C₆-alkyl oroptionally substituted C₃-C₈-cycloalkyl, to a reductive amination tofurnish compounds XXIII. Typical conditions for the reductive aminationare: Reacting ketone XX with an amine H₂NR⁵ to yield the correspondingimine which is reduced to amine XIII with a reducing agent reagent suchas Na(CN)BH₃. The reaction from ketone XX to amine XXIII may also becarried out as a one pot procedure.

For obtaining compounds in which R^(7a) and R^(7b) are optionallysubstituted alkyl, optionally substituted cycloalkyl, optionallysubstituted alkenyl or optionally substituted alkynyl, carbonylcompounds such as XX, in which R⁸ corresponds to R^(7a) which isoptionally substituted C₁-C₆-alkyl, optionally substitutedC₃-C₈-cycloalkyl, optionally substituted C₂-C₆-alkenyl or optionallysubstituted C₂-C₆-alkynyl, is reacted with a Grignard reagentR^(7b)—MgHal, where Hal is Cl, Br or I, or an organolithium compoundR^(7b)—Li, where R^(7b) is optionally substituted C₁-C₆-alkyl,optionally substituted C₃-C₈-cycloalkyl, optionally substitutedC₂-C₆-alkenyl or optionally substituted C₂-C₆-alkynyl, to obtain analcohol of formula XXIV.

Alcohol XXIV can then be converted into amine XXV via the correspondingazide, as described, for example, in Organic Letters, 2001, 3(20),3145-3148.

If desired, this can be converted into compounds I wherein R⁵ and R⁶ aredifferent from hydrogen, for example by standard alkylation reactions.

Compounds I wherein A is a group A³, wherein R^(7a) is optionallysubstituted alkyl, alkenyl, alkynyl, cycloalkyl or CN and R^(7b) ishydrogen, can be prepared by converting an aldehyde XVIII into an imineXXVI by reaction with an amine derivative NH₂R⁶, wherein R⁶ istert-butyl sulfinyl, or, for preparing a compound with R^(7a)═CN,tosylate.

This imine is then reacted with a compound H—R^(7a) in an additionreaction under conditions as described for example in J. Am. Chem. Soc.2009, 3850-3851 and the references cited therein, or, for introducing CNas a group R^(7a), Chemistry—A European Journal 2009, 15, 11642-11659.

Compounds I wherein A is a group A³, wherein both R^(7a) and R^(7b) areoptionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or CN, can beprepared analogously by converting a ketone XX, wherein R⁸ is has themeaning desired for R^(7b) and is optionally substituted alkyl, alkenyl,alkynyl, cycloalkyl or CN, into an imine by reaction with an aminederivative NH₂R⁶, wherein R⁶ is tert-butyl sulfinyl, or, for preparing acompound with R^(7a)═CN, tosylate.

This imine is then reacted with a compound H—R^(7a) in an additionreaction under conditions as described for example in J. Org. Chem.2002, 67, 7819-7832 and the references cited therein, or, forintroducing CN as a group R^(7a), Chemistry—A European Journal 2009, 15,11642-11659.

If desired, R⁶ can then be removed to yield an amino group NH₂.

Compounds I wherein A is A⁴ can be prepared by standard ring couplingreactions. For example, compounds, wherein A⁴ is an N-bound heterocyclicring can be prepared by reacting a compound I′ or I″ wherein A′ is Cl,Br or I with the respective ring A⁴-H (H being on the nitrogen ring atomto be coupled) under Ullmann coupling conditions, such as described, forexample, in WO 2007/075459. Typically, copper(I) iodide or copper(I)oxide and a ligand such as 1,2-cyclohexyldiamine is used, see forexample Kanemasa et al., European Journal of Organic Chemistry, 2004,695-709. If A′ is F, the reaction is typically run in a polar aproticsolvent such as N,N-dimethylformamide, N,N-dimethylacetamide orN-methylpyrrolidone, and in the presence of an inorganic base such assodium, potassium or cesium carbonate.

Compounds, wherein A⁴ is a C-bound heterocyclic ring can be prepared byreacting a compound I′ or I″ wherein A′ is Br or I with the boronic acidof the respective ring A⁴-B(OH)₂ or the boronate ester of the respectivering A⁴-B(OR₂) under Suzuki reaction conditions via Pd-catalyzed crosscoupling, such as described, for example, in WO 2007/075459. A typicalcatalyst is tetrakis(triphenylphosphine)palladium(0). Solvents such astetrahydrofuran, acetonitrile, diethyl ether and dioxane are suitable.The boronic acids A⁴-B(OH)₂ are either commercially available or can beprepared by known methods. Other methods for introduction of theheterocyclic groups A⁴ are the Heck, Stille, Kumada and Buchwald-Hartwigcoupling procedures; see for example Tetrahedron, 2004, 60, 8991-9016.

As a rule, the compounds of formula (I) including their stereoisomers,salts, and N-oxides, and their precursors in the synthesis process, canbe prepared by the methods described above. If individual compounds cannot be prepared via the above-described routes, they can be prepared byderivatization of other compounds (I) or the respective precursor or bycustomary modifications of the synthesis routes described. For example,in individual cases, certain compounds of formula (I) can advantageouslybe prepared from other compounds of formula (I) by derivatization, e.g.by ester hydrolysis, amidation, esterification, ether cleavage,olefination, reduction, oxidation and the like, or by customarymodifications of the synthesis routes described.

The reaction mixtures are worked up in the customary manner, for exampleby mixing with water, separating the phases, and, if appropriate,purifying the crude products by chromatography, for example on aluminaor on silica gel. Some of the intermediates and end products may beobtained in the form of colorless or pale brown viscous oils which arefreed or purified from volatile components under reduced pressure and atmoderately elevated temperature. If the intermediates and end productsare obtained as solids, they may be purified by recrystallization ortrituration.

Due to their excellent activity, the compounds of the present inventionmay be used for controlling invertebrate pests.

Accordingly, the present invention also provides a method forcontrolling invertebrate pests which method comprises treating thepests, their food supply, their habitat or their breeding ground or acultivated plant, plant propagation materials (such as seed), soil,area, material or environment in which the pests are growing or maygrow, or the materials, cultivated plants, plant propagation materials(such as seed), soils, surfaces or spaces to be protected from pestattack or infestation with a pesticidally effective amount of a compoundof the present invention or a composition as defined above.

Preferably, the method of the invention serves for protecting plantpropagation material (such as seed) and the plant which grows therefromfrom invertebrate pest attack or infestation and comprises treating theplant propagation material (such as seed) with a pesticidally effectiveamount of a compound of the present invention as defined above or with apesticidally effective amount of an agricultural composition as definedabove and below. The method of the invention is not limited to theprotection of the “substrate” (plant, plant propagation materials, soilmaterial etc.) which has been treated according to the invention, butalso has a preventive effect, thus, for example, according protection toa plant which grows from a treated plant propagation materials (such asseed), the plant itself not having been treated.

In the sense of the present invention, “invertebrate pests” arepreferably selected from arthropods and nematodes, more preferably fromharmful insects, arachnids and nematodes, and even more preferably frominsects, acarids and nematodes. In the sense of the present invention,“invertebrate pests” are most preferably insects.

The invention further provides an agricultural composition for combatinginvertebrate pests, which comprises such an amount of at least onecompound according to the invention and at least one inert liquid and/orsolid agronomically acceptable carrier that has a pesticidal action and,if desired, at least one surfactant.

Such a composition may comprise a single active compound of the presentinvention or a mixture of several active compounds of the presentinvention. The composition according to the present invention maycomprise an individual isomer or mixtures of isomers or a salt as wellas individual tautomers or mixtures of tautomers.

The compounds of the present invention, including their salts,stereoisomers and tautomers, are in particular suitable for efficientlycontrolling arthropodal pests such as arachnids, myriapedes and insectsas well as nematodes. They are especially suitable for efficientlycombating or controlling the following pests:

Insects from the order of the lepidopterans (Lepidoptera), for exampleAgrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsiagemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius,Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneurafumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydiapomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella,Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella,Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholithafunebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens,Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea,Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria,Laphygma exigua, Leucoptera coffeella, Leucoptera scitella,Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis,Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosomaneustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis,Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalerabucephala, Phthorimaea operculella, Phyllocnistis citrella, Pierisbrassicae, Pieris rapae, Plathypena scabra, Plutella xylostella,Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta,Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda,Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa,Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis; beetles(Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotesobscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomusgrandis, Anthonomus pomorum, Aphthona euphoridae, Athoushaemorrhoidalis, Atomaria linearis, Blastophagus piniperda, Blitophagaundata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscusbetulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata,Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis,Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp., Diabroticalongicornis, Diabrotica semipunctata, Diabrotica 12-punctata Diabroticaspeciosa, Diabrotica virgifera, Epilachna varivestis, Epitrixhirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hyperabrunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lemamelanopus, Leptinotarsa decemlineata, Limonius californicus,Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus,Melolontha hippocastani, Melolontha melolontha, Oulema oryzae,Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae,Phyllobius pyri, Phyllotreta chrysocephala, Phyllophaga sp.,Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata,Popillia japonica, Sitona lineatus and Sitophilus granaria;

flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedesvexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians,Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anophelesleucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphoravicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax,Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysopsatlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobiaanthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus,Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culisetamelanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Deliaantique, Delia coarctata, Delia platura, Delia radicum, Dermatobiahominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilusintestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes,Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris,Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconopstorrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Luciliacuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus,Mayetiola destructor, Musca autumnalis, Musca domestica, Muscinastabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomyahysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata,Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophoradiscolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella,Sarcophaga haemorrhoidalis, Sarcophaga spp., Simulium vittatum, Stomoxyscalcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, andTabanus similis, Tipula oleracea, and Tipula paludosa;thrips (Thysanoptera), e.g. Dichromothrips corbetti, Dichromothripsssp., Frankliniella fusca, Frankliniella occidentalis, Frankliniellatritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thripstabaci,

termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes,Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus,Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermesgrassei, Termes natalensis, and Coptotermes formosanus;

cockroaches (Blattaria—Blattodea), e.g. Blattella germanica, Blattellaasahinae, Periplaneta americana, Periplaneta japonica, Periplanetabrunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blattaorientalis;

bugs, aphids, leafhoppers, whiteflies, scale insects, cicadas(Hemiptera), e.g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltisnotatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygasterintegriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lyguslineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubeainsularis, Thyanta perditor, Acyrthosiphon onobrychis, Adelges laricis,Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphisgossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphissambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisia argentifolii,Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae,Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni,Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis,Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola,Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri,Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphumavenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae,Melanaphis pyrarius, Metopolophium dirhodum, Myzus persicae, Myzusascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri,Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida,Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus,Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum,Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneuralanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxopteraaurantiiand, Viteus vitifolii, Cimex lectularius, Cimex hemipterus,Reduvius senilis, Triatoma spp., and Arilus critatus;

ants, bees, wasps, sawflies (Hymenoptera), e.g. Athalia rosae, Attacephalotes, Atta capiguara, Atta cephalotes, Atta laevigata, Attarobusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampaminuta, Hoplocampa testudinea, Lasius niger, Monomorium pharaonis,Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsisxyloni, Pogonomyrmex barbatus, Pogonomyrmex californicus, Pheidolemegacephala, Dasymutilla occidentalis, Bombus spp., Vespula squamosa,Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica,Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Camponotusfloridanus, and Linepithema humile;

crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica,Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus,Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes,Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana,Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus,Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis,Kraussaria angulifera, Calliptamus italicus, Chortoicetes terminifera,and Locustana pardalina;

arachnoidea, such as arachnids (Acarina), e.g. of the familiesArgasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum,Amblyomma variegatum, Ambryomma maculatum, Argas persicus, Boophilusannulatus, Boophilus decoloratus, Boophilus microplus, Dermacentorsilvarum, Dermacentor andersoni, Dermacentor variabilis, Hyalommatruncatum, Ixodes ricinus, Ixodes rubicundus, Ixodes scapularis, Ixodesholocyclus, Ixodes pacificus, Ornithodorus moubata, Ornithodorus hermsi,Ornithodorus turicata, Ornithonyssus bacoti, Otobius megnini,Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus sanguineus,Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei,and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrataoleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemuspallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such asBrevipalpus phoenicis; Tetranychidae spp. such as Tetranychuscinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychustelarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, andOligonychus pratensis; Araneida, e.g. Latrodectus mactans, andLoxosceles reclusa;

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis,Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllusfasciatus,

silverfish, firebrat (Thysanura), e.g. Lepisma saccharina and Thermobiadomestica,

centipedes (Chilopoda), e.g. Scutigera coleoptrata,

millipedes (Diplopoda), e.g. Narceus spp.,

Earwigs (Dermaptera), e.g. forficula auricularia,

lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanuscorporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis,Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthusstramineus and Solenopotes capillatus.

Collembola (springtails), e.g. Onychiurus ssp.

The compounds of the present invention, including their salts,stereoisomers and tautomers, are also suitable for controllingnematodes:plant parasitic nematodes such as root knot nematodes,Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, andother Meloidogyne species; cyst-forming nematodes, Globoderarostochiensis and other Globodera species; Heterodera avenae, Heteroderaglycines, Heterodera schachtii, Heterodera trifolii, and otherHeterodera species; Seed gall nematodes, Anguina species; Stem andfoliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimuslongicaudatus and other Belonolaimus species; Pine nematodes,Bursaphelenchus xylophilus and other Bursaphelenchus species; Ringnematodes, Criconema species, Criconemella species, Criconemoidesspecies, Mesocriconema species; Stem and bulb nematodes, Ditylenchusdestructor, Ditylenchus dipsaci and other Ditylenchus species; Awlnematodes, Dolichodorus species; Spiral nematodes, Heliocotylenchusmulticinctus and other Helicotylenchus species; Sheath and sheathoidnematodes, Hemicycliophora species and Hemicriconemoides species;Hirshmanniella species; Lance nematodes, Hoploaimus species; falserootknot nematodes, Nacobbus species; Needle nematodes, Longidoruselongatus and other Longidorus species; Lesion nematodes, Pratylenchusneglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchusgoodeyi and other Pratylenchus species; Burrowing nematodes, Radopholussimilis and other Radopholus species; Reniform nematodes, Rotylenchusrobustus and other Rotylenchus species; Scutellonema species; Stubbyroot nematodes, Trichodorus primitivus and other Trichodorus species,Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni,Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrusnematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; andother plant parasitic nematode species.

The compounds of the present invention, including their salts,stereoisomers and tautomers, are particularly useful for controllinginsects, preferably sucking or piercing and chewing and biting insectssuch as insects from the genera Lepidoptera, Coleoptera and Hemiptera,in particular Lepidoptera, Coleoptera and true bugs.

The compounds of the present invention, including their salts,stereoisomers and tautomers, are moreover useful for controlling insectsof the orders Thysanoptera, Diptera (especially flies, mosquitos),Hymenoptera (especially ants) and Isoptera (especially termites.

The compounds of the present invention, including their salts,stereoisomers and tautomers, are particularly useful for controllinginsects of the orders Lepidoptera and Coleoptera.

The invention also relates to agrochemical compositions comprising anauxiliary and at least one compound I according to the invention.

An agrochemical composition comprises a pesticidally effective amount ofa compound I. The term “effective amount” denotes an amount of thecomposition or of the compounds I, which is sufficient for controllingharmful fungi on cultivated plants or in the protection of materials andwhich does not result in a substantial damage to the treated plants.Such an amount can vary in a broad range and is dependent on variousfactors, such as the species to be controlled, the treated cultivatedplant or material, the climatic conditions and the specific compound Iused.

The compounds I, their N-oxides and salts can be converted intocustomary types of agrochemical compositions, e.g. solutions, emulsions,suspensions, dusts, powders, pastes, granules, pressings, capsules, andmixtures thereof. Examples for composition types are suspensions (e.g.SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW,EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powdersor dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT),granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN),as well as gel formulations for the treatment of plant propagationmaterials such as seeds (e.g. GF). These and further compositions typesare defined in the “Catalogue of pesticide formulation types andinternational coding system”, Technical Monograph No. 2, 6^(th) Ed. May2008, CropLife International.

The compositions are prepared in a known manner, such as described byMollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001;or Knowles, New developments in crop protection product formulation,Agrow Reports DS243, T&F Inform a, London, 2005.

Suitable auxiliaries are solvents, liquid carriers, solid carriers orfillers, surfactants, dispersants, emulsifiers, wetters, adjuvants,solubilizers, penetration enhancers, protective colloids, adhesionagents, thickeners, humectants, repellents, attractants, feedingstimulants, compatibilizers, bactericides, anti-freezing agents,anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents,such as mineral oil fractions of medium to high boiling point, e.g.kerosene, diesel oil; oils of vegetable or animal origin; aliphatic,cyclic and aromatic hydrocarbons, e.g. toluene, paraffin,tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol,propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones,e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acidesters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides,e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixturesthereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates,silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite,diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate,magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers,e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas;products of vegetable origin, e.g. cereal meal, tree bark meal, woodmeal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic,cationic, nonionic and amphoteric surfactants, block polymers,polyelectrolytes, and mixtures thereof.

Such surfactants can be used as emusifier, dispersant, solubilizer,wetter, penetration enhancer, protective colloid, or adjuvant. Examplesof surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers &Detergents, McCutcheon's Directories, Glen Rock, USA, 2008(International Ed. or North American Ed.).

Suitable anionic surfactants are alkali, alkaline earth or ammoniumsalts of sulfonates, sulfates, phosphates, carboxylates, and mixturesthereof. Examples of sulfonates are alkylarylsulfonates,diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates,sulfonates of fatty acids and oils, sulfonates of ethoxylatedalkylphenols, sulfonates of alkoxylated arylphenols, sulfonates ofcondensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes,sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates orsulfosuccinamates. Examples of sulfates are sulfates of fatty acids andoils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols,or of fatty acid esters. Examples of phosphates are phosphate esters.Examples of carboxylates are alkyl carboxylates, and carboxylatedalcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acidamides, amine oxides, esters, sugar-based surfactants, polymericsurfactants, and mixtures thereof. Examples of alkoxylates are compoundssuch as alcohols, alkylphenols, amines, amides, arylphenols, fatty acidsor fatty acid esters which have been alkoxylated with 1 to 50equivalents. Ethylene oxide and/or propylene oxide may be employed forthe alkoxylation, preferably ethylene oxide. Examples of N-substitutedfatty acid amides are fatty acid glucamides or fatty acid alkanolamides.Examples of esters are fatty acid esters, glycerol esters ormonoglycerides. Examples of sugar-based surfactants are sorbitans,ethoxylated sorbitans, sucrose and glucose esters oralkylpolyglucosides. Examples of polymeric surfactants are home- orcopolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for examplequaternary ammonium compounds with one or two hydrophobic groups, orsalts of long-chain primary amines. Suitable amphoteric surfactants arealkylbetains and imidazolines. Suitable block polymers are blockpolymers of the A-B or A-B-A type comprising blocks of polyethyleneoxide and polypropylene oxide, or of the A-B-C type comprising alkanol,polyethylene oxide and polypropylene oxide. Suitable polyelectrolytesare polyacids or polybases. Examples of polyacids are alkali salts ofpolyacrylic acid or polyacid comb polymers. Examples of polybases arepolyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even nopesticidal activity themselves, and which improve the biologicalperformance of the compound I on the target. Examples are surfactants,mineral or vegetable oils, and other auxilaries. Further examples arelisted by Knowles, Adjuvants and additives, Agrow Reports DS256, T&FInforma UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum,carboxymethylcellulose), anorganic clays (organically modified orunmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives suchas alkylisothiazolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol,urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, andsalts of fatty acids.

Suitable colorants (e.g. in red, blue, or green) are pigments of lowwater solubility and water-soluble dyes. Examples are inorganiccolorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) andorganic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinylpyrrolidons,polyvinylacetates, polyvinyl alcohols, polyacrylates, biological orsynthetic waxes, and cellulose ethers.

Examples for composition types and their preparation are:

i) Water-Soluble concentrates (SL, LS)

10-60 wt % of a compound I according to the invention and 5-15 wt %wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/orin a water-soluble solvent (e.g. alcohols) ad 100 wt %. The activesubstance dissolves upon dilution with water.

ii) Dispersible Concentrates (DC)

5-25 wt % of a compound I according to the invention and 1-10 wt %dispersant (e.g. polyvinylpyrrolidone) are dissolved in organic solvent(e.g. cyclohexanone) ad 100 wt %. Dilution with water gives adispersion.

iii) Emulsifiable Concentrates (EC)

15-70 wt % of a compound I according to the invention and 5-10 wt %emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oilethoxylate) are dissolved in water-insoluble organic solvent (e.g.aromatic hydrocarbon) ad 100 wt %. Dilution with water gives anemulsion.

iv) Emulsions (EW, EO, ES)

5-40 wt % of a compound I according to the invention and 1-10 wt %emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oilethoxylate) are dissolved in 20-40 wt % water-insoluble organic solvent(e.g. aromatic hydrocarbon). This mixture is introduced into water ad100 wt % by means of an emulsifying machine and made into a homogeneousemulsion. Dilution with water gives an emulsion.

v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt % of a compound I according to theinvention are comminuted with addition of 2-10 wt % dispersants andwetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt % thickener (e.g. xanthan gum) and water ad 100 wt % to give afine active substance suspension. Dilution with water gives a stablesuspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.

vi) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)

50-80 wt % of a compound I according to the invention are ground finelywith addition of dispersants and wetting agents (e.g. sodiumlignosulfonate and alcohol ethoxylate) ad 100 wt % and prepared aswater-dispersible or water-soluble granules by means of technicalappliances (e.g. extrusion, spray tower, fluidized bed). Dilution withwater gives a stable dispersion or solution of the active substance.

vii) Water-Dispersible Powders and Water-Soluble Powders (WP, SP, WS)

50-80 wt % of a compound I according to the invention are ground in arotor-stator mill with addition of 1-5 wt % dispersants (e.g. sodiumlignosulfonate), 1-3 wt % wetting agents (e.g. alcohol ethoxylate) andsolid carrier (e.g. silica gel) ad 100 wt %. Dilution with water gives astable dispersion or solution of the active substance.

viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt % of a compound I according to theinvention are comminuted with addition of 3-10 wt % dispersants (e.g.sodium lignosulfonate), 1-5 wt % thickener (e.g. carboxymethylcellulose)and water ad 100 wt % to give a fine suspension of the active substance.Dilution with water gives a stable suspension of the active substance.

iv) Microemulsion (ME)

5-20 wt % of a compound I according to the invention are added to 5-30wt % organic solvent blend (e.g. fatty acid dimethylamide andcyclohexanone), 10-25 wt % surfactant blend (e.g. alkohol ethoxylate andarylphenol ethoxylate), and water ad 100%. This mixture is stirred for 1h to produce spontaneously a thermodynamically stable microemulsion.

iv) Microcapsules (CS)

An oil phase comprising 5-50 wt % of a compound I according to theinvention, 0-40 wt % water insoluble organic solvent (e.g. aromatichydrocarbon), 2-15 wt % acrylic monomers (e.g. methylmethacrylate,methacrylic acid and a di- or triacrylate) are dispersed into an aqueoussolution of a protective colloid (e.g. polyvinyl alcohol). Radicalpolymerization initiated by a radical initiator results in the formationof poly(meth)acrylate microcapsules. Alternatively, an oil phasecomprising 5-50 wt % of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and anisocyanate monomer (e.g. diphenylmethene-4,4′-diisocyanatae) aredispersed into an aqueous solution of a protective colloid (e.g.polyvinyl alcohol). The addition of a polyamine (e.g.hexamethylenediamine) results in the formation of a polyureamicrocapsules. The monomers amount to 1-10 wt %. The wt % relate to thetotal CS composition.

ix) Dustable Powders (DP, DS)

1-10 wt % of a compound I according to the invention are ground finelyand mixed intimately with solid carrier (e.g. finely divided kaolin) ad100 wt %.

x) Granules (GR, FG)

0.5-30 wt % of a compound I according to the invention is ground finelyand associated with solid carrier (e.g. silicate) ad 100 wt %.Granulation is achieved by extrusion, spray-drying or the fluidized bed.

xi) Ultra-Low Volume Liquids (UL)

1-50 wt % of a compound I according to the invention are dissolved inorganic solvent (e.g. aromatic hydrocarbon) ad 100 wt %.

The compositions types i) to xi) may optionally comprise furtherauxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt % anti-freezingagents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt % colorants.

The agrochemical compositions generally comprise between 0.01 and 95%,preferably between 0.1 and 90%, and in particular between 0.5 and 75%,by weight of active substance. The active substances are employed in apurity of from 90% to 100%, preferably from 95% to 100% (according toNMR spectrum).

Solutions for seed treatment (LS), Suspoemulsions (SE), flowableconcentrates (FS), powders for dry treatment (DS), water-dispersiblepowders for slurry treatment (WS), water-soluble powders (SS), emulsions(ES), emulsifiable concentrates (EC) and gels (GF) are usually employedfor the purposes of treatment of plant propagation materials,particularly seeds. The compositions in question give, aftertwo-to-tenfold dilution, active substance concentrations of from 0.01 to60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-usepreparations. Application can be carried out before or during sowing.Methods for applying compound I and compositions thereof, respectively,on to plant propagation material, especially seeds include dressing,coating, pelleting, dusting, soaking and in-furrow application methodsof the propagation material. Preferably, compound I or the compositionsthereof, respectively, are applied on to the plant propagation materialby a method such that germination is not induced, e.g. by seed dressing,pelleting, coating and dusting.

When employed in plant protection, the amounts of active substancesapplied are, depending on the kind of effect desired, from 0.001 to 2 kgper ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.

In treatment of plant propagation materials such as seeds, e.g. bydusting, coating or drenching seed, amounts of active substance of from0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to100 g and most preferably from 5 to 100 g, per 100 kilogram of plantpropagation material (preferably seeds) are generally required. Whenused in the protection of materials or stored products, the amount ofactive substance applied depends on the kind of application area and onthe desired effect. Amounts customarily applied in the protection ofmaterials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of activesubstance per cubic meter of treated material.

Various types of oils, wetters, adjuvants, fertilizer, ormicronutrients, and further pesticides (e.g. herbicides, insecticides,fungicides, growth regulators, safeners) may be added to the activesubstances or the compositions comprising them as premix or, ifappropriate not until immediately prior to use (tank mix). These agentscan be admixed with the compositions according to the invention in aweight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

The user applies the composition according to the invention usually froma predosage device, a knapsack sprayer, a spray tank, a spray plane, oran irrigation system. Usually, the agrochemical composition is made upwith water, buffer, and/or further auxiliaries to the desiredapplication concentration and the ready-to-use spray liquor or theagrochemical composition according to the invention is thus obtained.Usually, 20 to 2000 liters, preferably 50 to 400 liters, of theready-to-use spray liquor are applied per hectare of agricultural usefularea.

According to one embodiment, individual components of the compositionaccording to the invention such as parts of a kit or parts of a binaryor ternary mixture may be mixed by the user himself in a spray tank andfurther auxiliaries may be added, if appropriate. In a furtherembodiment, either individual components of the composition according tothe invention or partially premixed components, e.g. componentscomprising compounds I and/or active substances from the groups M) or F)(see below), may be mixed by the user in a spray tank and furtherauxiliaries and additives may be added, if appropriate.

In a further embodiment, either individual components of the compositionaccording to the invention or partially premixed components, e.g.components comprising compounds I and/or active substances from thegroups M) or F) (see below), can be applied jointly (e.g. after tankmix) or consecutively.

The following categorized list M of pesticides represents insecticidalmixture partners, which are, whenever possible, classified according tothe Insecticide Resistance Action Committee (IRAC), and together withwhich the compounds according to the present invention may be used. Thecombined use of the compounds of the present invention with thefollowing pesticides may result in potential synergistic effects. Thefollowing examples of insecticidal mixing partners are provided with theintention to illustrate the possible combinations, but not to impose anylimitation to the obtainable mixtures:

-   M.1 Acetylcholine esterase (AChE) inhibitors from the class of-   M.1A carbamates, for example aldicarb, alanycarb, bendiocarb,    benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran,    carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb,    isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb,    propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and    triazamate; or from the class of-   M.1B organophosphates, for example acephate, azamethiphos,    azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos,    chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl,    coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP,    dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,    ethoprophos, famphur, fenamiphos, fenitrothion, fenthion,    fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl    O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion,    mecarbam, methamidophos, methidathion, mevinphos, monocrotophos,    naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl,    phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,    pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos,    pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos,    terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and    vamidothion;-   M.2. GABA-gated chloride channel antagonists such as:-   M.2A cyclodiene organochlorine compounds, as for example endosulfan    or chlordane; or-   M.2B fiproles (phenylpyrazoles), as for example ethiprole, fipronil,    flufiprole, pyrafluprole and pyriprole;-   M.3 Sodium channel modulators from the class of-   M.3A pyrethroids, for example acrinathrin, allethrin, d-cis-trans    allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin    S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin,    beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin,    cypermethrin, alpha-cypermethrin, beta-cypermethrin,    theta-cypermethrin, zetacypermethrin, cyphenothrin, deltamethrin,    empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate,    flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin,    meperfluthrin, metofluthrin, permethrin, phenothrin, prallethrin,    profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen,    tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin and    transfluthrin; or-   M.3B sodium channel modulators such as DDT or methoxychlor;-   M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class    of-   M.4A neonicotinoids, for example acteamiprid, chlothianidin,    dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam;    or-   M.4B nicotine.-   M.5 Nicotinic acetylcholine receptor allosteric activators from the    class of spinosyns, for example spinosad or spinetoram;-   M.6 Chloride channel activators from the class of avermectins and    milbemycins, for example abamectin, emamectin benzoate, ivermectin,    lepimectin or milbemectin;-   M.7 Juvenile hormone mimics, such as-   M.7A juvenile hormone analogues as hydroprene, kinoprene and    methoprene; or others as-   M.7B fenoxycarb, or-   M.7C pyriproxyfen;-   M.8 miscellaneous non-specific (multi-site) inhibitors, for example-   M.8A alkyl halides as methyl bromide and other alkyl halides, or-   M.8B chloropicrin, or-   M.8C sulfuryl fluoride, or-   M.8D borax, or-   M.8E tartar emetic;-   M.9 Selective homopteran feeding blockers, for example-   M.9B pymetrozine, or-   M.9C flonicamid;-   M.10 Mite growth inhibitors, for example-   M.10A clofentezine, hexythiazox and diflovidazin, or-   M.10B etoxazole;-   M.11 Microbial disruptors of insect midgut membranes, for example    bacillus thuringiensis or bacillus sphaericus and the insecticdal    proteins they produce such as bacillus thuringiensis subsp.    israelensis, bacillus sphaericus, bacillus thuringiensis subsp.    aizawai, bacillus thuringiensis subsp. kurstaki and bacillus    thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1Ab,    Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1;-   M.12 Inhibitors of mitochondrial ATP synthase, for example-   M.12A diafenthiuron, or-   M.12B organotin miticides such as azocyclotin, cyhexatin or    fenbutatin oxide, or M.12C propargite, or-   M.12D tetradifon;-   M.13 Uncouplers of oxidative phosphorylation via disruption of the    proton gradient, for example chlorfenapyr, DNOC or sulfluramid;-   M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, for    example nereistoxin analogues as bensultap, cartap hydrochloride,    thiocyclam or thiosultap sodium;-   M.15 Inhibitors of the chitin biosynthesis type 0, such as    benzoylureas as for example bistrifluoron, chlorfluazuron,    diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron,    novaluron, noviflumuron, teflubenzuron or triflumuron;-   M.16 Inhibitors of the chitin biosynthesis type 1, as for example    buprofezin;-   M.17 Moulting disruptors, Dipteran, as for example cyromazine;-   M.18 Ecdyson receptor agonists such as diacylhydrazines, for example    methoxyfenozide, tebufenozide, halofenozide, fufenozide or    chromafenozide;-   M.19 Octopamin receptor agonists, as for example amitraz;-   M.20 Mitochondrial complex III electron transport inhibitors, for    example-   M.20A hydramethylnon, or-   M.20B acequinocyl, or-   M.20C fluacrypyrim;-   M.21 Mitochondrial complex I electron transport inhibitors, for    example-   M.21A METI acaricides and insecticides such as fenazaquin,    fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad,    or-   M.21B rotenone;-   M.22 Voltage-dependent sodium channel blockers, for example-   M.22A indoxacarb, or-   M.22B metaflumizone;-   M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic    and Tetramic acid derivatives, for example spirodiclofen,    spiromesifen or spirotetramat;-   M.24 Mitochondrial complex IV electron transport inhibitors, for    example-   M.24A phosphine such as aluminium phosphide, calcium phosphide,    phosphine or zinc phosphide, or-   M.24B cyanide.-   M.25 Mitochondrial complex II electron transport inhibitors, such as    beta-ketonitrile derivatives, for example cyenopyrafen or    cyflumetofen;-   M.28 Ryanodine receptor-modulators from the class of diamides, as    for example flubendiamide, chloranthraniliprole (Rynaxypyr®),    cyanthraniliprole (Cyazypyr®), or    the phthalamide compounds-   M.28.1:    (R)-3-Chlor-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid    and-   M.28.2:    (S)-3-Chlor-N1-{2-methyl-4-[1,2,2,2-tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid,    or the compound-   M.28.3:    3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chlorpyridin-2-yl)-1H-pyrazole-5-carboxamide,    or the compound-   M.28.4:    methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarboxylate;

M.X insecticidal active compounds of unknown or uncertain mode ofaction, as for example azadirachtin, amidoflumet, benzoximate,bifenazate, bromopropylate, chinomethionat, cryolite, dicofol,flufenerim, flometoquin, fluensulfone, flupyradifurone, piperonylbutoxide, pyridalyl, pyrifluquinazon, sulfoxaflor, or the compound

-   M.X.1:    4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzamide,    or the compound-   M.X.2: cyclopropaneacetic acid,    1,1′-[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[[(2-cyclopropylacetyl)oxy]methyl]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-[2-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-3,6-diyl]ester,    or the compound-   M.X.3:    11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one,    or the compound-   M.X.4:    3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one,    or the compound-   M.X.5:    1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine,    or actives on basis of bacillus firmus (Votivo, 1-1582).

The commercially available compounds of the group M listed above may befound in The Pesticide Manual, 15th Edition, C. D. S. Tomlin, BritishCrop Protection Council (2011) among other publications.

The phthalamides M.28.1 and M.28.2 are both known from WO 2007/101540.The anthranilamide M.28.3 has been described in WO2005/077943. Thehydrazide compound M.28.4 has been described in WO 2007/043677.—Thequinoline derivative flometoquin is shown in WO2006/013896. Theaminofuranone compounds flupyradifurone is known from WO 2007/115644.The sulfoximine compound sulfoxaflor is known from WO2007/149134. Theisoxazoline compound M.X.1 has been described in WO2005/085216. Thepyripyropene derivative M.X.2 has been described in WO 2006/129714. Thespiroketal-substituted cyclic ketoenol derivative M.X.3 is known fromWO2006/089633 and the biphenyl-substituted spirocyclic ketoenolderivative M.X.4 from WO2008/067911. Finally triazoylphenylsulfide likeM.X.5 have been described in WO2006/043635 and biological control agentson basis of bacillus firmus in WO2009/124707.

The following list F of active substances, in conjunction with which thecompounds according to the invention can be used, is intended toillustrate the possible combinations but does not limit them:

-   F.I) Respiration Inhibitors-   F.I-1) Inhibitors of complex III at Qo site (e.g. strobilurins)    strobilurins: azoxystrobin, coumethoxystrobin, coumoxystrobin,    dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl,    metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin,    pyrametostrobin, pyraoxystrobin, pyribencarb,    triclopyricarb/chlorodincarb, trifloxystrobin,    2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid    methyl ester and 2    (2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)phenyl)-2-methoxyimino-N    methyl-acetamide;-   oxazolidinediones and imidazolinones: famoxadone, fenamidone;-   F.I-2) Inhibitors of complex II (e.g. carboxamides):-   carboxanilides: benodanil, bixafen, boscalid, carboxin, fenfuram,    fenhexamid, fluopyram, flutolanil, furametpyr, isopyrazam,    isotianil, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane,    tecloftalam, thifluzamide, tiadinil, 2-amino-4    methyl-thiazole-5-carboxanilide, N-(3′,4′,5′ trifluorobiphenyl-2    yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4 carboxamide,    N-(4′-trifluoromethylthiobiphenyl-2-yl)-3 difluoromethyl-1-methyl-1H    pyrazole-4-carboxamide and    N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5    fluoro-1H-pyrazole-4 carboxamide;-   F.I-3) Inhibitors of complex III at Qi site: cyazofamid, amisulbrom;-   F.I-4) Other respiration inhibitors (complex I, uncouplers)-   diflumetorim; tecnazen; ferimzone; ametoctradin; silthiofam;-   nitrophenyl derivates: binapacryl, dinobuton, dinocap, fluazinam,    nitrthal-isopropyl, organometal compounds: fentin salts, such as    fentin-acetate, fentin chloride or fentin hydroxide;-   F.II) Sterol biosynthesis inhibitors (SBI fungicides)-   F.II-1) C14 demethylase inhibitors (DMI fungicides, e.g. triazoles,    imidazoles)-   triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole,    difenoconazole, diniconazole, diniconazole-M, epoxiconazole,    fenbuconazole, fluquinconazole, flusilazole, flutriafol,    hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil,    paclobutrazole, penconazole, propiconazole, prothioconazole,    simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol,    triticonazole, uniconazole; imidazoles: imazalil, pefurazoate,    oxpoconazole, prochloraz, triflumizole; pyrimidines, pyridines and    piperazines: fenarimol, nuarimol, pyrifenox, triforine;-   F.II-2) Delta 14-reductase inhitors (Amines, e.g. morpholines,    piperidines) morpholines: aldimorph, dodemorph, dodemorph-acetate,    fenpropimorph, tridemorph;-   piperidines: fenpropidin, piperalin;-   spiroketalamines: spiroxamine;-   F.II-3) Inhibitors of 3-keto reductase: hydroxyanilides: fenhexamid;-   F.III) Nucleic acid synthesis inhibitors-   F.III-1) RNA, DNA synthesis-   phenylamides or acyl amino acid fungicides: benalaxyl, benalaxyl-M,    kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl;-   isoxazoles and iosothiazolones: hymexazole, octhilinone;-   F.III-2) DNA topisomerase inhibitors: oxolinic acid;-   F.III-3) Nucleotide metabolism (e.g. adenosin-deaminase)-   hydroxy (2-amino)-pyrimidines: bupirimate;-   F.IV) Inhibitors of cell division and or cytoskeleton-   F.IV-1) Tubulin inhibitors: benzimidazoles and thiophanates:    benomyl, carbendazim, fuberidazole, thiabendazole,    thiophanate-methyl;-   triazolopyrimidines: 5-chloro-7    (4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5a]pyrimidine-   F.IV-2) Other cell division inhibitors benzamides and phenyl    acetamides: diethofencarb, ethaboxam, pencycuron, fluopicolide,    zoxamide;-   F.IV-3) Actin inhibitors: benzophenones: metrafenone;-   F.V) Inhibitors of amino acid and protein synthesis-   F.V-1) Mmethionine synthesis inhibitors (anilino-pyrimidines)-   anilino-pyrimidines: cyprodinil, mepanipyrim, nitrapyrin,    pyrimethanil;-   F.V-2) Protein synthesis inhibitors (anilino-pyrimidines)    antibiotics: blasticidin-S, kasugamycin, kasugamycin    hydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin,    polyoxine, validamycin A;-   F.VI) Signal transduction inhibitors-   F.VI-1) MAP/Histidine kinase inhibitors (e.g. anilino-pyrimidines)-   dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin;-   phenylpyrroles: fenpiclonil, fludioxonil;-   F.VI-2) G protein inhibitors: quinolines: quinoxyfen;-   F.VII) Lipid and membrane synthesis inhibitors-   F.VII-1) Phospholipid biosynthesis inhibitors-   organophosphorus compounds: edifenphos, iprobenfos, pyrazophos;-   dithiolanes: isoprothiolane;-   F.VII-2) Lipid peroxidation-   aromatic hydrocarbons: dicloran, quintozene, tecnazene,    tolclofos-methyl, biphenyl, chloroneb, etridiazole;-   F.VII-3) Carboxyl acid amides (CAA fungicides)-   cinnamic or mandelic acid amides: dimethomorph, flumorph,    mandiproamid, pyrimorph;-   valinamide carbamates: benthiavalicarb, iprovalicarb, pyribencarb,    valifenalate and    N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl)carbamic    acid-(4-fluorophenyl)ester;-   F.VII-4) Compounds affecting cell membrane permeability and fatty    acides carbamates: propamocarb, propamocarb-hydrochlorid-   F.VIII) Inhibitors with Multi Site Action-   F.VIII-1) Inorganic active substances: Bordeaux mixture, copper    acetate, copper hydroxide, copper oxychloride, basic copper sulfate,    sulfur;-   F.VIII-2) Thio- and dithiocarbamates: ferbam, mancozeb, maneb,    metam, methasulphocarb, metiram, propineb, thiram, zineb, ziram;-   F.VIII-3) Organochlorine compounds (e.g. phthalimides, sulfamides,    chloronitriles): anilazine, chlorothalonil, captafol, captan,    folpet, dichlofluanid, dichlorophen, flusulfamide,    hexachlorobenzene, pentachlorphenole and its salts, phthalide,    tolylfluanid,    N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;-   F.VIII-4) Guanidines: guanidine, dodine, dodine free base,    guazatine, guazatineacetate, iminoctadine, iminoctadine-triacetate,    iminoctadine-tris(albesilate);-   F.VIII-5) Ahtraquinones: dithianon;-   F.IX) Cell wall synthesis inhibitors-   F.IX-1) Inhibitors of glucan synthesis: validamycin, polyoxin B;-   F.IX-2) Melanin synthesis inhibitors: pyroquilon, tricyclazole,    carpropamide, dicyclomet, fenoxanil;-   F.X) Plant defence inducers-   F.X-1) Salicylic acid pathway: acibenzolar-S-methyl;-   F.X-2) Others: probenazole, isotianil, tiadinil,    prohexadione-calcium;-   phosphonates: fosetyl, fosetyl-aluminum, phosphorous acid and its    salts;-   F.XI) Unknown mode of action:-   bronopol, chinomethionat, cyflufenamid, cymoxanil, dazomet,    debacarb, diclomezine, difenzoquat, difenzoquat-methylsulfate,    diphenylamin, flumetover, flusulfamide, flutianil, methasulfocarb,    oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide,    2-butoxy-6-iodo-3-propylchromen-4-one,    N-(cyclopropylmethoxyimino-(6-difluoromethoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl    acetamide,    N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N    methyl formamidine,    N′(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl    formamidine,    N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl    formamidine, N′-(5-difluoromethyl-2    methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl    formamidine,    2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic    acid methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amide,    2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic    acid methyl-(R)-1,2,3,4-tetrahydro-naphthalen-1-yl-amide,    methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl    ester and    N-Methyl-2-{1-[(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-4-thiazolecarboxamide,    3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine,    pyrisoxazole,    5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro-pyrazole-1    carbothioic acid S-allyl ester,    N-(6-methoxy-pyridin-3-yl)cyclopropanecarboxylic acid amide,    5-chloro-1(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole,    2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide;-   F.XI) Growth regulators:-   abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine,    brassinolide, butralin, chlormequat (chlormequat chloride), choline    chloride, cyclanilide, daminozide, dikegulac, dimethipin,    2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol,    fluthiacet, forchlorfenuron, gibberellic acid, inabenfide,    indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat    (mepiquat chloride), naphthaleneacetic acid, N 6 benzyladenine,    paclobutrazol, prohexadione (prohexadione-calcium), prohydrojasmon,    thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5 tri    iodobenzoic acid, trinexapac-ethyl and uniconazole;-   F.XII) Biological control agents-   antifungal biocontrol agents: Bacillus substilis strain with NRRL    No. B-21661 (e.g. RHAPSODY®, SERENADE® MAX and SERENADE® ASO from    AgraQuest, Inc., USA.), Bacillus pumilus strain with NRRL No.    B-30087 (e.g. SONATA® and BALLAD® Plus from AgraQuest, Inc., USA),    Ulocladium oudemansii (e.g. the product BOTRYZEN from BotriZen Ltd.,    New Zealand), Chitosan (e.g. ARMOUR-ZEN from BotriZen Ltd., New    Zealand).

The invertebrate pest (also referred to as “animal pest”), i.e. theinsects, arachnids and nematodes, the plant, soil or water in which theplant is growing or may grow can be contacted with the compounds of thepresent invention or composition(s) comprising them by any applicationmethod known in the art. As such, “contacting” includes both directcontact (applying the compounds/compositions directly on theinvertebrate pest or plant—typically to the foliage, stem or roots ofthe plant) and indirect contact (applying the compounds/compositions tothe locus of the invertebrate pest or plant).

The compounds of the present invention or the pesticidal compositionscomprising them may be used to protect growing plants and crops fromattack or infestation by animal pests, especially insects, acaridae orarachnids by contacting the plant/crop with a pesticidally effectiveamount of compounds of the present invention. The term “crop” refersboth to growing and harvested crops.

The compounds of the present invention and the compositions comprisingthem are particularly important in the control of a multitude of insectson various cultivated plants, such as cereal, root crops, oil crops,vegetables, spices, ornamentals, for example seed of durum and otherwheat, barley, oats, rye, maize (fodder maize and sugar maize/sweet andfield corn), soybeans, oil crops, crucifers, cotton, sunflowers,bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet,eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks,pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons,Brassica species, melons, beans, peas, garlic, onions, carrots, tuberousplants such as potatoes, sugar cane, tobacco, grapes, petunias,geranium/pelargoniums, pansies and impatiens.

The compounds of the present invention are employed as such or in formof compositions by treating the insects or the plants, plant propagationmaterials, such as seeds, soil, surfaces, materials or rooms to beprotected from insecticidal attack with an insecticidally effectiveamount of the active compounds. The application can be carried out bothbefore and after the infection of the plants, plant propagationmaterials, such as seeds, soil, surfaces, materials or rooms by theinsects.

Moreover, invertebrate pests may be controlled by contacting the targetpest, its food supply, habitat, breeding ground or its locus with apesticidally effective amount of compounds of the present invention. Assuch, the application may be carried out before or after the infectionof the locus, growing crops, or harvested crops by the pest.

The compounds of the present invention can also be applied preventivelyto places at which occurrence of the pests is expected.

The compounds of the present invention may be also used to protectgrowing plants from attack or infestation by pests by contacting theplant with a pesticidally effective amount of compounds of the presentinvention. As such, “contacting” includes both direct contact (applyingthe compounds/compositions directly on the pest and/or plant—typicallyto the foliage, stem or roots of the plant) and indirect contact(applying the compounds/compositions to the locus of the pest and/orplant).

“Locus” means a habitat, breeding ground, plant, seed, soil, area,material or environment in which a pest or parasite is growing or maygrow.

In general, “pesticidally effective amount” means the amount of activeingredient needed to achieve an observable effect on growth, includingthe effects of necrosis, death, retardation, prevention, and removal,destruction, or otherwise diminishing the occurrence and activity of thetarget organism. The pesticidally effective amount can vary for thevarious compounds/compositions used in the invention. A pesticidallyeffective amount of the compositions will also vary according to theprevailing conditions such as desired pesticidal effect and duration,weather, target species, locus, mode of application, and the like.

In the case of soil treatment or of application to the pests dwellingplace or nest, the quantity of active ingredient ranges from 0.0001 to500 g per 100 m², preferably from 0.001 to 20 g per 100 m².

Customary application rates in the protection of materials are, forexample, from 0.01 g to 1000 g of active compound per m² treatedmaterial, desirably from 0.1 g to 50 g per m².

Insecticidal compositions for use in the impregnation of materialstypically contain from 0.001 to 95 weight %, preferably from 0.1 to 45weight %, and more preferably from 1 to 25 weight % of at least onerepellent and/or insecticide.

For use in treating crop plants, the rate of application of the activeingredients of this invention may be in the range of 0.1 g to 4000 g perhectare, desirably from 5 g to 500 g per hectare, more desirably from 5g to 200 g per hectare.

The compounds of the present invention are effective through bothcontact (via soil, glass, wall, bed net, carpet, plant parts or animalparts), and ingestion (bait, or plant part).

The compounds of the present invention may also be applied againstnon-crop insect pests, such as ants, termites, wasps, flies, mosquitos,crickets, or cockroaches. For use against said non-crop pests, compoundsof the present invention are preferably used in a bait composition.

The bait can be a liquid, a solid or a semisolid preparation (e.g. agel). Solid baits can be formed into various shapes and forms suitableto the respective application e.g. granules, blocks, sticks, disks.Liquid baits can be filled into various devices to ensure properapplication, e.g. open containers, spray devices, droplet sources, orevaporation sources. Gels can be based on aqueous or oily matrices andcan be formulated to particular necessities in terms of stickyness,moisture retention or aging characteristics. The bait employed in thecomposition is a product, which is sufficiently attractive to inciteinsects such as ants, termites, wasps, flies, mosquitos, crickets etc.or cockroaches to eat it. The attractiveness can be manipulated by usingfeeding stimulants or sex pheromones. Food stimulants are chosen, forexample, but not exclusively, from animal and/or plant proteins (meat-,fish- or blood meal, insect parts, egg yolk), from fats and oils ofanimal and/or plant origin, or mono-, oligo- or polyorganosaccharides,especially from sucrose, lactose, fructose, dextrose, glucose, starch,pectin or even molasses or honey. Fresh or decaying parts of fruits,crops, plants, animals, insects or specific parts thereof can also serveas a feeding stimulant. Sex pheromones are known to be more insectspecific. Specific pheromones are described in the literature and areknown to those skilled in the art.

For use in bait compositions, the typical content of active ingredientis from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to5% weight % of active ingredient.

Formulations of compounds of the present invention as aerosols (e.g inspray cans), oil sprays or pump sprays are highly suitable for thenon-professional user for controlling pests such as flies, fleas, ticks,mosquitos or cockroaches. Aerosol recipes are preferably composed of theactive compound, solvents such as lower alcohols (e.g. methanol,ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethylketone), paraffin hydrocarbons (e.g. kerosenes) having boiling ranges ofapproximately 50 to 250° C., dimethylformamide, N-methylpyrrolidone,dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene,water, furthermore auxiliaries such as emulsifiers such as sorbitolmonooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fattyalcohol ethoxylate, perfume oils such as ethereal oils, esters of mediumfatty acids with lower alcohols, aromatic carbonyl compounds, ifappropriate stabilizers such as sodium benzoate, amphoteric surfactants,lower epoxides, triethyl orthoformate and, if required, propellants suchas propane, butane, nitrogen, compressed air, dimethyl ether, carbondioxide, nitrous oxide, or mixtures of these gases.

The oil spray formulations differ from the aerosol recipes in that nopropellants are used.

For use in spray compositions, the content of active ingredient is from0.001 to 80 weights %, preferably from 0.01 to 50 weight % and mostpreferably from 0.01 to 15 weight %.

The compounds of the present invention and its respective compositionscan also be used in mosquito and fumigating coils, smoke cartridges,vaporizer plates or long-term vaporizers and also in moth papers, mothpads or other heat-independent vaporizer systems.

Methods to control infectious diseases transmitted by insects (e.g.malaria, dengue and yellow fever, lymphatic filariasis, andleishmaniasis) with compounds of the present invention and itsrespective compositions also comprise treating surfaces of huts andhouses, air spraying and impregnation of curtains, tents, clothingitems, bed nets, tsetse-fly trap or the like. Insecticidal compositionsfor application to fibers, fabric, knitgoods, nonwovens, nettingmaterial or foils and tarpaulins preferably comprise a mixture includingthe insecticide, optionally a repellent and at least one binder.Suitable repellents for example are N,N-Diethyl-meta-toluamide (DEET),N,N-diethylphenylacetamide (DEPA),1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine,(2-hydroxymethylcyclohexyl)acetic acid lactone, 2-ethyl-1,3-hexandiol,indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insectcontrol such as{(+/−)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate(Esbiothrin), a repellent derived from or identical with plant extractslike limonene, eugenol, (+)-Eucamalol (1), (−)-1-epi-eucamalol or crudeplant extracts from plants like Eucalyptus maculata, Vitex rotundifolia,Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogannartdus (citronella). Suitable binders are selected for example frompolymers and copolymers of vinyl esters of aliphatic acids (such as suchas vinyl acetate and vinyl versatate), acrylic and methacrylic esters ofalcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methylacrylate, mono- and di-ethylenically unsaturated hydrocarbons, such asstyrene, and aliphatic diens, such as butadiene.

The impregnation of curtains and bednets is done in general by dippingthe textile material into emulsions or dispersions of the insecticide orspraying them onto the nets. The compounds of the present invention andtheir compositions can be used for protecting wooden materials such astrees, board fences, sleepers, etc. and buildings such as houses,outhouses, factories, but also construction materials, furniture,leathers, fibers, vinyl articles, electric wires and cables etc. fromants and/or termites, and for controlling ants and termites from doingharm to crops or human being (e.g. when the pests invade into houses andpublic facilities). The compounds of the present invention are appliednot only to the surrounding soil surface or into the under-floor soil inorder to protect wooden materials but it can also be applied to lumberedarticles such as surfaces of the under-floor concrete, alcove posts,beams, plywoods, furniture, etc., wooden articles such as particleboards, half boards, etc. and vinyl articles such as coated electricwires, vinyl sheets, heat insulating material such as styrene foams,etc. In case of application against ants doing harm to crops or humanbeings, the ant controller of the present invention is applied to thecrops or the surrounding soil, or is directly applied to the nest ofants or the like.

The compounds of the present invention are also suitable for thetreatment of plant propagation material, especially seeds, in order toprotect them from insect pest, in particular from soil-living insectpests and the resulting plant's roots and shoots against soil pests andfoliar insects.

The compounds of the present invention are particularly useful for theprotection of the seed from soil pests and the resulting plant's rootsand shoots against soil pests and foliar insects. The protection of theresulting plant's roots and shoots is preferred.

More preferred is the protection of resulting plant's shoots frompiercing and sucking insects, wherein the protection from aphids is mostpreferred.

The present invention therefore comprises a method for the protection ofseeds from insects, in particular from soil insects and of theseedlings' roots and shoots from insects, in particular from soil andfoliar insects, said method comprising contacting the seeds beforesowing and/or after pregermination with a compound of the presentinvention, including a salt thereof. Particularly preferred is a method,wherein the plant's roots and shoots are protected, more preferably amethod, wherein the plants shoots are protected form piercing andsucking insects, most preferably a method, wherein the plants shoots areprotected from aphids.

The term seed embraces seeds and plant propagules of all kinds includingbut not limited to true seeds, seed pieces, suckers, corms, bulbs,fruit, tubers, grains, cuttings, cut shoots and the like and means in apreferred embodiment true seeds.

The term seed treatment comprises all suitable seed treatment techniquesknown in the art, such as seed dressing, seed coating, seed dusting,seed soaking and seed pelleting.

The present invention also comprises seeds coated with or containing theactive compound.

The term “coated with and/or containing” generally signifies that theactive ingredient is for the most part on the surface of the propagationproduct at the time of application, although a greater or lesser part ofthe ingredient may penetrate into the propagation product, depending onthe method of application. When the said propagation product is(re)planted, it may absorb the active ingredient.

Suitable seed is seed of cereals, root crops, oil crops, vegetables,spices, ornamentals, for example seed of durum and other wheat, barley,oats, rye, maize (fodder maize and sugar maize/sweet and field corn),soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice,oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes,grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash,cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species,melons, beans, peas, garlic, onions, carrots, tuberous plants such aspotatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums,pansies and impatiens.

In addition, the active compound may also be used for the treatmentseeds from plants, which tolerate the action of herbicides or fungicidesor insecticides owing to breeding, including genetic engineeringmethods.

For example, the active compound can be employed in treatment of seedsfrom plants, which are resistant to herbicides from the group consistingof the sulfonylureas, imidazolinones, glufosinate-ammonium orglyphosate-isopropylammonium and analogous active substances (see forexample, EP-A 242 236, EP-A 242 246) (WO 92/00377) (EP-A 257 993, U.S.Pat. No. 5,013,659) or in transgenic crop plants, for example cotton,with the capability of producing Bacillus thuringiensis toxins (Bttoxins) which make the plants resistant to certain pests (EP-A 142 924,EP-A 193 259),

Furthermore, the active compound can be used also for the treatment ofseeds from plants, which have modified characteristics in comparisonwith existing plants consist, which can be generated for example bytraditional breeding methods and/or the generation of mutants, or byrecombinant procedures). For example, a number of cases have beendescribed of recombinant modifications of crop plants for the purpose ofmodifying the starch synthesized in the plants (e.g. WO 92/11376, WO92/14827, WO 91/19806) or of transgenic crop plants having a modifiedfatty acid composition (WO 91/13972).

The seed treatment application of the active compound is carried out byspraying or by dusting the seeds before sowing of the plants and beforeemergence of the plants.

Compositions which are especially useful for seed treatment are e.g.:

A Soluble concentrates (SL, LS)

D Emulsions (EW, EO, ES)

E Suspensions (SC, OD, FS)

F Water-dispersible granules and water-soluble granules (WG, SG)

G Water-dispersible powders and water-soluble powders (WP, SP, WS)

H Gel-Formulations (GF)

I Dustable powders (DP, DS)

Conventional seed treatment formulations include for example flowableconcentrates FS, solutions LS, powders for dry treatment DS, waterdispersible powders for slurry treatment WS, water-soluble powders SSand emulsion ES and EC and gel formulation GF. These formulations can beapplied to the seed diluted or undiluted. Application to the seeds iscarried out before sowing, either directly on the seeds or after havingpregerminated the latter.

In a preferred embodiment a FS formulation is used for seed treatment.Typically, a FS formulation may comprise 1-800 g/l of active ingredient,1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l ofbinder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent,preferably water.

Especially preferred FS formulations of compounds of the presentinvention for seed treatment usually comprise from 0.1 to 80% by weight(1 to 800 g/l) of the active ingredient, from 0.1 to 20% by weight (1 to200 g/l) of at least one surfactant, e.g. 0.05 to 5% by weight of awetter and from 0.5 to 15% by weight of a dispersing agent, up to 20% byweight, e.g. from 5 to 20% of an anti-freeze agent, from 0 to 15% byweight, e.g. 1 to 15% by weight of a pigment and/or a dye, from 0 to 40%by weight, e.g. 1 to 40% by weight of a binder (sticker/adhesion agent),optionally up to 5% by weight, e.g. from 0.1 to 5% by weight of athickener, optionally from 0.1 to 2% of an anti-foam agent, andoptionally a preservative such as a biocide, antioxidant or the like,e.g. in an amount from 0.01 to 1% by weight and a filler/vehicle up to100% by weight.

Seed Treatment formulations may additionally also comprise binders andoptionally colorants.

Binders can be added to improve the adhesion of the active materials onthe seeds after treatment. Suitable binders are homo- and copolymersfrom alkylene oxides like ethylene oxide or propylene oxide,polyvinylacetate, polyvinylalcohols, polyvinylpyrrolidones, andcopolymers thereof, ethylene-vinyl acetate copolymers, acrylic homo- andcopolymers, polyethyleneamines, polyethyleneamides andpolyethyleneimines, polysaccharides like celluloses, tylose and starch,polyolefin homo- and copolymers like olefin/maleic anhydride copolymers,polyurethanes, polyesters, polystyrene homo and copolymers.

Optionally, also colorants can be included in the formulation. Suitablecolorants or dyes for seed treatment formulations are Rhodamin B, C.I.Pigment Red 112, C.I. Solvent Red 1, pigment blue 15:4, pigment blue15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigmentyellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigmentred 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigmentorange 34, pigment orange 5, pigment green 36, pigment green 7, pigmentwhite 6, pigment brown 25, basic violet 10, basic violet 49, acid red51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10,basic red 108.

Examples of a Gelling Agent is Carrageen (Satiagel®)

In the treatment of seed, the application rates of the compounds of thepresent invention are generally from 0.01 g to 10 kg per 100 kg of seed,preferably from 0.05 g to 5 kg per 100 kg of seed, more preferably from0.1 g to 1000 g per 100 kg of seed and in particular from 0.1 g to 200 gper 100 kg of seed.

The invention therefore also relates to seed comprising a compound ofthe present invention, including an agriculturally useful salt of it, asdefined herein. The amount of the compound of the present invention,including an agriculturally useful salt thereof will in general varyfrom 0.01 g to 10 kg per 100 kg of seed, preferably from 0.05 g to 5 kgper 100 kg of seed, in particular from 0.1 g to 1000 g per 100 kg ofseed. For specific crops such as lettuce the rate can be higher.

Methods which can be employed for treating the seed are, in principle,all suitable seed treatment and especially seed dressing techniquesknown in the art, such as seed coating (e.g. seed pelleting), seeddusting and seed imbibition (e.g. seed soaking). Here, “seed treatment”refers to all methods that bring seeds and the compounds of the presentinvention into contact with each other, and “seed dressing” to methodsof seed treatment which provide the seeds with an amount of thecompounds of the present invention, i.e. which generate a seedcomprising a compound of the present invention. In principle, thetreatment can be applied to the seed at any time from the harvest of theseed to the sowing of the seed. The seed can be treated immediatelybefore, or during, the planting of the seed, for example using the“planter's box” method. However, the treatment may also be carried outseveral weeks or months, for example up to 12 months, before plantingthe seed, for example in the form of a seed dressing treatment, withouta substantially reduced efficacy being observed.

Expediently, the treatment is applied to unsown seed. As used herein,the term “unsown seed” is meant to include seed at any period from theharvest of the seed to the sowing of the seed in the ground for thepurpose of germination and growth of the plant.

Specifically, a procedure is followed in the treatment in which the seedis mixed, in a suitable device, for example a mixing device for solid orsolid/liquid mixing partners, with the desired amount of seed treatmentformulations, either as such or after previous dilution with water,until the composition is distributed uniformly on the seed. Ifappropriate, this is followed by a drying step.

The compounds of the present invention, including their stereoisomers,veterinarily acceptable salts or N-oxides, are in particular alsosuitable for being used for combating parasites in and on animals.

An object of the present invention is therfore also to provide newmethods to control parasites in and on animals. Another object of theinvention is to provide safer pesticides for animals. Another object ofthe invention is further to provide pesticides for animals that may beused in lower doses than existing pesticides. And another object of theinvention is to provide pesticides for animals, which provide a longresidual control of the parasites.

The invention also relates to compositions comprising a parasiticidallyeffective amount of compounds of the present invention, including theirstereoisomers, veterinarily acceptable salts or N-oxides, and anacceptable carrier, for combating parasites in and on animals.

The present invention also provides a method for treating, controlling,preventing and protecting animals against infestation and infection byparasites, which comprises orally, topically or parenterallyadministering or applying to the animals a parasiticidally effectiveamount of a compound of the present invention, including itsstereoisomers, veterinarily acceptable salts or N-oxides, or acomposition comprising it.

The invention also provides a process for the preparation of acomposition for treating, controlling, preventing or protecting animalsagainst infestation or infection by parasites which comprises aparasiticidally effective amount of a compound of the present invention,including its stereoisomers, veterinarily acceptable salts or N-oxides,or a composition comprising it.

Activity of compounds against agricultural pests does not suggest theirsuitability for control of endo- and ectoparasites in and on animalswhich requires, for example, low, non-emetic dosages in the case of oralapplication, metabolic compatibility with the animal, low toxicity, anda safe handling.

Surprisingly it has now been found that compounds of formula (I) andtheir stereoisomers, veterinarily acceptable salts, tautomers andN-oxides, are suitable for combating endo- and ectoparasites in and onanimals.

The compounds of the present invention, especially compounds of formula(I) and their stereoisomers, veterinarily acceptable salts, tautomersand N-oxides, and compositions comprising them are preferably used forcontrolling and preventing infestations of and infections in animalsincluding warm-blooded animals (including humans) and fish.

They are for example suitable for controlling and preventinginfestations and infections in mammals such as cattle, sheep, swine,camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats,water buffalo, donkeys, fallow deer and reindeer, and also in furbearinganimals such as mink, chinchilla and raccoon, birds such as hens, geese,turkeys and ducks and fish such as fresh- and salt-water fish such astrout, carp and eels. Compounds of the present invention, includingtheir stereoisomers, veterinarily acceptable salts or N-oxides, andcompositions comprising them are preferably used for controlling andpreventing infestations and infections in domestic animals, such as dogsor cats.

Infestations in warm-blooded animals and fish include, but are notlimited to, lice, biting lice, ticks, nasal bots, keds, biting flies,muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoesand fleas.

The compounds of the present invention, including their stereoisomers,veterinarily acceptable salts or N-oxides, and compositions comprisingthem are suitable for systemic and/or non-systemic control of ecto-and/or endoparasites. They are active against all or some stages ofdevelopment.

The compounds of the present invention are especially useful forcombating parasites of the following orders and species, respectively:fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis,Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllusfasciatus, cockroaches (Blattaria—Blattodea), e.g. Blattella germanica,Blattella asahinae, Periplaneta americana, Periplaneta japonica,Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae,and Blatta orientalis, flies, mosquitoes (Diptera), e.g. Aedes aegypti,Aedes albopictus, Aedes vexans, Anastrepha ludens, Anophelesmaculipennis, Anopheles crucians, Anopheles albimanus, Anophelesgambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus,Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana,Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysopssilacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobiaanthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus,Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culisetamelanura, Dermatobia hominis, Fannia canicularis, Gasterophilusintestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes,Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris,Hippelates spp., Hypoderma lineata, Leptoconops torrens, Luciliacaprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansoniaspp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomusargentipes, Psorophora columbiae, Psorophora discolor, Prosimuliummixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum,Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola,and Tabanus similis, lice (Phthiraptera), e.g. Pediculus humanuscapitis, Pediculus humanus corporis, Pthirus pubis, Haematopinuseurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis,Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus.ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodesscapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalussanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyommaamericanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorusturicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacotiand Dermanyssus gallinae,

Actinedida (Prostigmata) und Acaridida (Astigmata) e.g. Acarapis spp.,Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp.,Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.,Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp.,Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp.,Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptesspp, Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduviussenilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Ariluscritatus,

Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp.,Phtirus spp., and Solenopotes spp,

Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenoponspp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp.,Lepikentron spp., Trichodectes spp., and Felicola spp,

Roundworms Nematoda:

Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae(Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp,Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp,Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus,Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus,Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp.,Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanusspp., Chabertia spp., Stephanurus dentatus, Syngamus trachea,Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp.,Metastrongylus spp., Muellerius capillaris, Protostrongylus spp.,Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylusabstrusus, and Dioctophyma renale,

Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascarissuum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis(Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., andOxyuris equi,

Camallanida, e.g. Dracunculus medinensis (guinea worm)

Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocercaspp., Dirofilari spp.a, Dipetalonema spp., Setaria spp., Elaeophoraspp., Spirocerca lupi, and Habronema spp.,

Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp.,Macracanthorhynchus hirudinaceus and Oncicola spp,

Planarians (Plathelminthes):

Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimusspp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis,Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp.,and Nanocyetes spp,

Cercomeromorpha, in particular Cestoda (Tapeworms), e.g.Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidiumcaninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp.,Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp.,Anoplocephala spp., and Hymenolepis spp.

The present invention relates to the therapeutic and the non-therapeuticuse of compounds of the present invention and compositions comprisingthem for controlling and/or combating parasites in and/or on animals.The compounds of the present invention and compositions comprising themmay be used to protect the animals from attack or infestation byparasites by contacting them with a parasiticidally effective amount ofcompounds of the present invention and compositions containing them.

The compounds of the present invention and compositions comprising themcan be effective through both contact (via soil, glass, wall, bed net,carpet, blankets or animal parts) and ingestion (e.g. baits). As such,“contacting” includes both direct contact (applying the pesticidalmixtures/compositions containing the compounds of the present inventiondirectly on the parasite, which may include an indirect contact at itslocus-P, and optionally also administrating the pesticidalmixtures/composition directly on the animal to be protected) andindirect contact (applying the compounds/compositions to the locus ofthe parasite). The contact of the parasite through application to itslocus is an example of a non-therapeutic use of compounds of the presentinvention. “Locus-P” as used above means the habitat, food supply,breeding ground, area, material or environment in which a parasite isgrowing or may grow outside of the animal.

In general, “parasiticidally effective amount” means the amount ofactive ingredient needed to achieve an observable effect on growth,including the effects of necrosis, death, retardation, prevention, andremoval, destruction, or otherwise diminishing the occurrence andactivity of the target organism. The parasiticidally effective amountcan vary for the various compounds/compositions of the presentinvention. A parasiticidally effective amount of the compositions willalso vary according to the prevailing conditions such as desiredparasiticidal effect and duration, target species, mode of application,and the like.

The compounds of the present invention can also be applied preventivelyto places at which occurrence of the pests or parasites are expected.

Administration can be carried out both prophylactically andtherapeutically.

Administration of the active compounds is carried out directly or in theform of suitable preparations, orally, topically/dermally orparenterally.

The compounds of the invention have a distinctly shorter half live inthe soil and thus are significantly less persistent than isoxazolinecompounds of similar structure and insecticidal activity.

EXAMPLES

The present invention is now illustrated in further details by thefollowing examples, without imposing any limitation thereto.

Preparation Examples

Compounds can be characterized e.g. by coupled High Performance LiquidChromatography/mass spectrometry (HPLC/MS), by ¹H-NMR and/or by theirmelting points.

Analytical HPLC column:

Method A: Analytical UPLC column: RP-18 column Chromolith Speed ROD,50×4.6 mm, from Merck KgaA, Germany). Elution: acetonitrile+0.1%trifluoroacetic acid (TFA)/water+0.1% trifluoroacetic acid (TFA) in aratio of from 5:95 to 95:5 in 5 minutes at 40° C. Flow: 1.8 mL/min.MS-method: ESI positive.

Method B: Analytical UPLC column: Phenomenex Kinetex 1.7 μm XB-C18 100A;50×2.1 mm from Phenomenex, Germany. Elution: acetonitrile+0.1%trifluoroacetic acid (TFA)/water+0.1% trifluoroacetic acid (TFA) in aratio from 5:95 to 100:0 in 1.5 min at 60° C. Flow: 0.8 mL/min to 1mL/min in 1.5 min. MS-method: ESI positive.

1H-NMR, respectively ¹³C-NMR: The signals are characterized by chemicalshift (ppm, δ [delta]) vs. tetramethylsilane, respectively CDCl₃ for¹³C-NMR, by their multiplicity and by their integral (relative number ofhydrogen atoms given). The following abbreviations are used tocharacterize the multiplicity of the signals: m=multiplett, q=quartett,t=triplett, d=doublet and s=singulett.

Abbreviations used are: h for hour(s), min for minute(s), r.t./roomtemperature for 20-25° C., THF for tetrahydrofuran, OAc for acetate.

C.1 Compound Examples 1

Compound examples 1-1 to 1-20 correspond to compounds of formula C.1:

wherein R^(2a), R^(2b), R^(2c), R⁴, and R⁶ of each synthesized compoundis defined in one row of table C.1 below.

The compounds were synthesized in analogy to Synthesis Example S.1.

TABLE C.1 HPLC-MS: Method, R_(t) (min) & [M + H]⁺ Ex. R^(2a), R^(2b),R^(2c) R⁴ R⁶ or 1H-NMR 1-1 Cl, H, Cl CH₃ NHC(═O)—NHCH₂CF₃ A 4.052 557.01-2 Cl, H, Cl CH₃ NHC(═O)—NHCH₃ A 4.420 489.1 1-3 Cl, H, Cl CH₃NHC(═O)—NH- 1H NMR (400 MHz, CDCl₃): δ 9.5 (cyclopropyl) (s, 1H), 8.0(s, 1H), 7.8 (d, 1H), 7.7- 7.5 (m, 2H), 7.4 (s, 1H), 7.3 (s, 2H), 6.2(s, 1H), 4.2 (d, 1H), 3.8 (d, 1H), 2.8-2.7 (m, 1H), 2.5 (s, 3H), 2.0-0.5(m, 4H) 1-4 Cl, H, Cl CH₃ NHC(═O)—NHCH₂- B 1.681 531.0 (cyclopropyl) 1-5Cl, H, Cl CH₃ NHC(═O)—NHCH₂CH₃ B 1.681 503.2 1-6 Cl, H, Cl CH₃NHC(═O)—NH₂ A 4.065 474.9 1-7 Cl, H, Cl Cl NHC(═O)—NHCH₃ B 1.446 509.01-8 Cl, H, Cl Cl NHC(═O)—NHCH₂CF₂H B 1.475 560.9 1-9 Cl, H, Cl ClNHC(═O)—NHCH₂CF₃ B 1.502 578.9 1-10 Cl, H, Cl Cl NHC(═O)—NHCH₂CH₃ B1.319 523.0 1-11 Cl, H, Cl Cl NH-(2-pyridyl) A 3.891 530.9 1-12 Cl, H,Cl Cl NHC(═O)—OCH₃ B 1.471 512.1 1-13 Cl, H, Cl Cl NHC(═O)—NHOCH₃ 1H NMR(400 MHz, CDCl₃): δ 8.5- 8.2 (m, 2H), 8.2 (s, 1H), 8.0 (d, 1H), 7.8 (s,1H), 7.7 (d, 1H), 7.4 (s, 1H), 7.3 (s, 2H), 4.2 (d, 1H), 3.8-3.9 (m, 4H)1-14 Cl, H, Cl Cl NHC(═S)—NHCH₃ B 1.509 527.1 1-15 Cl, H, Cl ClNHC(═O)—CH₂CH₃ A 4.466 509.9 1-16 Cl, H, Cl Cl N(CH₃)₂ B 1.687 480.11-17 Cl, Cl, Cl OCH₃ NHC(═O)—NHCH₃ B 1.448 540.8 1-18 Cl, Cl, Cl OCH₃NHC(═O)—NHCH₂CF₃ B 1.503 608.9 1-19 Cl, Cl, Cl OCH₃ NHC(═O)—NHCH₂CCH B1.459 564.8 1-20 Cl, H, Cl Cl OH 1H NMR (400 MHz, CDCl₃): δ 8.5 s, 1H),7.9 (d, 1H, 7.8 (s, 1H), 7.6 d, 1H), 7.5 (s, 1H, 7.4 (s, 1H), 7.3 s,2H), 4.2 (d, 1H, 3.8 (d, 1H)

C.2 Compound Examples 2

Compound examples 2-1 to 2-233 correspond to compounds of formula C.2:

wherein R^(2a), R^(2b), R^(2c), R⁴, and Y of each synthesized compoundis defined in one row of table C.2 below.

The compounds were synthesized in analogy to Synthesis Example S.2.

TABLE C.2 HPLC-MS: Method, R_(t) (min) & [M + H]⁺ Ex. R^(2a), R^(2b),R^(2c) R⁴ Y or 1H-NMR 2-1 Cl, H, Cl CH₃ NHCH₂C(═O)—NHCH₂CF₃ A 4.242572.0 2-2 Cl, H, Cl CH₃ NHCH₂C(═O)— B 1.348 530.1 NHCH₂(cyclopropyl) 2-3Cl, H, Cl CH₃ NHCH₂-(2-F—C₆H₄) B 1.521 541.0 2-4 Cl, H, Cl CH₃NHCH₂-(2-pyridyl) B 1.167 525.9 2-5 Cl, H, Cl CH₃ NH-(3-thiethanyl) B1.473 506.8 2-6 Cl, H, Cl CH₃ NHCH₂CF₃ B 1.487 515.0 2-7 Cl, H, Cl CH₃NHCH₂-(4-(OCH₃)—C₆H₄) B 1.508 554.9 2-8 Cl, H, Cl CH₃NHCH₂-(3-(OCH₃)—C₆H₄) B 1.518 553.1 2-9 Cl, H, Cl CH₃ NHCH₂-(2-thienyl)B 1.511 530.7 2-10 Cl, H, Cl CH₃ NHCH₂-(cyclopropyl) B 1.491 487.1 2-11Cl, H, Cl CH₃ NH-(1-oxo-thiethan-3-yl) B 1.307 521.1 2-12 Cl, H, Cl CH₃NHCH₂-(4-thiazolyl) B 1.396 530.0 2-13 Cl, H, Cl CH₃NH-(1,1-dioxo-thiethan-3-yl) A 4.172 537.0 2-14 Cl, H, Cl CH₃ H B 1.526418.0 2-15 Cl, H, Cl CH₃ NHCH₂—C₆H₅ B 1.501 523.3 2-16 Cl, H, Cl CH₃OCH₃ B 1.596 448.0 2-17 Cl, H, Cl F OH 1H NMR (400 MHz, CDCl₃): δ8.2-8.0 (m, 1H), 7.7-7.5 (m, 2H), 7.4 (s, 1H), 7.3 (s, 2H), 4.2 (d, 1H),3.9 (d, 1H) 2-18 Cl, H, Cl F NHCH₂C(═O)—NHCH₂CF₃ B 1.397 576.2 2-19 Cl,H, Cl F NHCH₂-(2-pyridyl) B 1.207 528.2 2-20 Cl, H, Cl FNH-(3-thiethanyl) B 1.479 509.1 2-21 Cl, H, Cl F NHCH₂CF₃ B 1.478 519.22-22 Cl, H, Cl F OCH₃ B 1.544 452.2 2-23 Cl, H, Cl FNH-(1,1-dioxo-thiethan-3-yl) B 1.361 541.2 2-24 Cl, H, Cl Cl OCH₃ B1.583 470.0 2-25 Cl, H, Cl Cl OH 1H NMR (400 MHz, CDCl₃): δ 8.1-8.0 (m,1H), 7.9 (s, 1H), 7.8- 7.7 (m, 1H), 7.4 (s, 1H), 7.3 (s, 2H), 4.2 (d,1H), 3.9 (d, 1H) 2-26 Cl, H, Cl Cl NHCH₂-(2-pyridyl) B 1.194 544.0 2-27Cl, H, Cl Cl NHCH₂C(═O)—NHCH₂CF₃ B 1.397 594.0 2-28 Cl, H, Cl ClNH-(3-thiethanyl) B 1.460 526.9 2-29 Cl, H, Cl Cl NHCH₂CF₃ B 1.462 536.82-30 Cl, H, Cl Cl NH-(1-oxo-thiethan-3-yl) B 1.310 543.0 2-31 Cl, H, ClCl pyrrolidin-1-yl B 1.514 509.1 2-32 Cl, H, Cl Cl NHCH₂-(4-thiazolyl) B1.412 552.0 2-33 Cl, H, Cl F NH-(1-oxo-thiethan-3-yl) B 1.304 526.9 2-34Cl, H, Cl F pyrrolidin-1-yl B 1.473 492.9 2-35 Cl, H, Cl ClNHCH₂-(3-pyridyl) B 1.162 545.9 2-36 Cl, H, Cl Cl H 1H NMR (400 MHz,CDCl₃): δ 10.5 (s, 1H), 8.0 (d, 1H), 7.8 (s, 1H), 7.7 (d, 1H), 7.4 (s,1H), 7.3 (s, 2H), 4.2 (d, 1H), 3.9 (d, 1H) 2-37 Cl, H, Cl ClNHCH₂-(4-pyridyl) B 1.150 544.2 2-38 Cl, H, Cl Cl NH—C₆H₅ B 1.508 530.92-39 Cl, H, Cl Cl NHCH₂-(6-Cl-pyrid-3-yl) B 1.447 580.0 2-40 Cl, H, ClCl NH-(1,1-dioxo-thiethan-3-yl) B 1.196 557.0 2-41 Cl, H, Cl FNHCH₂-(4-thiazolyl) B 1.396 534.0 2-42 Cl, H, Cl Cl NH-(3-pyridyl) B1.202 531.9 2-43 Cl, H, Cl CH₃ NHCH₂-(3,3-difluoro- B 1.466 537.3cyclobut-1-yl) 2-44 Cl, H, Cl Cl NH-(2-pyridyl) B 1.429 531.8 2-45 Cl,H, Cl Cl NH-(4-pyridyl) B 1.170 532.0 2-46 Cl, H, Cl CH₃NH—CH₂-(2-nitrophenyl) B 1.485 568.3 2-47 Cl, H, Cl ClN(CH₃)—CH₂-(2-pyridyl) B 1.314 560.0 2-48 Cl, H, Cl ClNHCH₂-(4-pyrimidyl) B 1.343 546.8 2-49 Cl, H, Cl Cl N(CH₂CH₃)—CH₂-(2- B1.338 573.8 pyridyl) 2-50 Cl, H, Cl Cl NHCH₂-(2-pyrimidyl) B 1.374 547.42-51 Cl, H, Cl CH₃ NHCH₂-(cyclobutyl) B 1.511 501.1 2-52 Cl, H, Cl CH₃NHCH₂-(cyclopentyl) B 1.546 516.8 2-53 Cl, H, Cl CH₃ NHCH₂-(2-pyrazinyl)B 1.353 525.0 2-54 Cl, H, Cl CH₃ NHCH₂-(3-pyridyl) B 1.128 524.3 2-55Cl, H, Cl CH₃ NHCH₂-(4-pyridyl) B 1.130 524.2 2-56 Cl, H, Cl CH₃NH-(2-pyridyl) B 1.351 510.3 2-57 Cl, H, Cl CH₃ NH-(3-pyridyl) B 1.183510.3 2-58 Cl, H, Cl CH₃ NH-(4-pyridyl) B 1.174 510.3 2-59 Cl, H, Cl CH₃NHCH₂-(2-pyrimidyl) B 1.355 525.3 2-60 Cl, H, Cl CH₃ NHCH₂-(4-pyrimidyl)B 1.331 525.3 2-61 Cl, H, Cl CH₃ NH—C₆H₅ B 1.514 509.3 2-62 Cl, H, ClCH₃ N(CH₃)—CH₂-(2-pyridyl) B 1.274 538.3 2-63 Cl, H, Cl CH₃N(CH₂CH₃)—CH₂-(2- B 1.305 552.3 pyridyl) 2-64 Cl, H, Cl CH₃N(CH₂CCH)—CH₂-(2- B 1.331 562.3 pyridyl) 2-65 Cl, H, Cl CH₃N(CH₃)—CH₂-(4-thiazolyl) B 1.438 544.3 2-66 Cl, H, Cl CH₃ N(CH₃)—OCH₃ B1.448 477.0 2-67 Cl, H, Cl CH₃ NH—CH₂-(2-oxazolyl) B 1.363 514.1 2-68Cl, H, Cl CH₃ NH-(3-oxetanyl) B 1.223 489.1 2-69 Cl, H, Cl CH₃pyrrolidin-1-yl B 1.463 487.3 2-70 Cl, H, Cl CH₃ azetidin-1-yl B 1.422474.8 2-71 Cl, H, Cl CH₃ NH-cyclobutyl B 1.467 487.0 2-72 Cl, H, Cl CH₃NH—CH₂-(3-isoxazolyl) B 1.383 514.1 2-73 Cl, H, Cl CH₃ N(CH₂CH₃)—CH₂-(4-B 1.467 558.2 thiazolyl) 2-74 Cl, H, Cl CH₃ NHCH₂-(2-thiazolyl) B 1.380530.2 2-75 Cl, H, Cl CH₃ aziridin-1-yl B 1.502 459.2 2-76 Cl, H, Cl CH₃morpholino B 1.408 503.0 2-77 Cl, H, Cl CH₃ thiazolidin-3-yl B 1.476505.1 2-78 Cl, H, Cl CH₃ thiomorpholino B 1.489 519.0 2-79 Cl, H, Cl CH₃1,1-dioxo-1,4-thiazinan-4- B 1.356 551.2 yl 2-80 Cl, H, Cl CH₃1-piperidyl B 1.533 501.3 2-81 Cl, H, Cl CH₃ NH-[1-cyano-cycloprop-1- B1.391 498.0 yl] 2-82 Cl, H, Cl CH₃ NH-(cyclopropyl) B 1.409 473.0 2-83Cl, H, Cl CH₃ NHCH₂CF₂H B 1.418 497.0 2-84 Cl, H, Cl CH₃ NHCH₂CH₂CF₃ B1.460 529.0 2-85 Cl, H, Cl CH₃ NHCH₂-[1-cyano- B 1.392 512.1cycloprop-1-yl] 2-86 Cl, H, Cl CH₃ NHCH₂CH₃ B 1.245 461.0 2-87 Cl, H, ClCH₃ NHCH₃ B 1.359 447.0 2-88 Cl, H, Cl CH₃ NHCH₂CCH B 1.396 471.0 2-89Cl, H, Cl CH₃ NHCH₂CH═CH₂ B 1.423 473.0 2-90 Cl, H, Cl CH₃NHCH₂CH₂CF═CF₂ B 1.477 541.0 2-91 Cl, H, Cl CH₃ NHCH(CH₃)₂ B 1.445 475.02-92 Cl, H, Cl CH₃ NHCH₂C(CH₃)₃ B 1.529 504.8 2-93 Cl, H, Cl CH₃NHCH₂CH₂CH₃ B 1.445 475.4 2-94 Cl, H, Cl CH₃ NHCH₂CH(CH₃)₂ B 1.487 489.02-95 Cl, H, Cl CH₃ NHCH₂CN B 1.365 472.0 2-96 Cl, H, Cl CH₃ NHCH(CF₃)₂ B1.546 583.0 2-97 Cl, H, Cl CH₃ NHCH₂CH₂SCH₂CH₃ B 1.476 521.0 2-98 Cl, H,Cl CH₃ NHC(CH₃)₂CH₂SCH₃ B 1.534 535.1 2-99 Cl, H, Cl CH₃ NHCH(CH₃)CF₃ B1.481 529.3 2-100 Cl, H, Cl CH₃ NH-(3,3-difluoro-cyclobut- B 1.451 523.31-yl 2-101 Cl, H, Cl CH₃ NHCH₂-(1,2,3-thiadiazol- B 1.386 532.7 4-yl)2-102 Cl, H, Cl CH₃ NHCH₂-(1,3,4-thiadiazol- B 1.334 531.0 2-yl) 2-103Cl, H, Cl CH₃ N═S[CH(CH₃)₂]₂ B 1.355 549.3 2-104 Cl, H, Cl CH₃N═S(CH₂CH₃)₂ B 1.308 521.3 2-105 Cl, H, Cl CH₃ NHCH₂-[2,2-dichloro- B1.510 557.2 cycloprop-1-yl] 2-106 Cl, H, Cl CH₃ NHCH₂-(1- B 1.120 527.3methylimidazol-2-yl) 2-107 Cl, H, Cl CH₃ NHCH₂-(5-oxazolyl) B 1.349514.3 2-108 Cl, H, Cl CH₃ NHCH₂CH₂SCH₃ B 1.544 507.0 2-109 Cl, H, Cl CH₃NHCH(CH₃)CH₂SCH₃ B 1.551 521.0 2-110 Cl, H, Cl CH₃ NHCH₂-(2-Cl—C₆H₄) B1.533 557.0 2-111 Cl, H, Cl CH₃ NHCH₂-(2-OCH₃ C₆H₄) B 1.501 557.0 2-112Cl, H, Cl CH₃ NHCH(CH₃)CH₂SO₂CH₃ B 1.340 553.0 2-113 Cl, H, Cl CH₃1-oxo-1,4-thiazinan-4-yl B 1.279 535.0 2-114 Cl, H, Cl CH₃N(CH₂CN) CH₂-(2- B 1.392 564.9 pyridyl) 2-115 Cl, H, Cl CH₃NHCH₂-(1-CH₃-pyrazol-3-yl) B 1.368 527.3 2-116 Cl, H, Cl CH₃NHCH₂-(2-CH₃-pyrazol-3-yl) B 1.364 527.3 2-117 Cl, H, Cl CH₃NHCH₂-(1-CH₃-imidazol- B 1.124 527.3 4-yl) 2-118 Cl, H, Cl CH₃NHCH₂-(4-oxazolyl) B 1.361 514.3 2-119 Cl, H, Cl CH₃ NHCH₂-(2-oxetanyl)B 1.376 503.3 2-120 Cl, H, Cl CH₃ NH-(3-tetrahydrofuranyl) B 1.358 503.02-121 Cl, H, Cl CH₃ NH-[(2-pyridyl)cycloprop-1-yl] B 1.234 550.1 2-122Cl, Cl, Cl CH₃ OC(CH₃)₃ 1H NMR (400 MHz, CDCl₃): δ 7.8 (d, 1H), 7.6-7.5(m, 1H), 7.4 (s, 2H), 4.2 (d, 1H), 3.9 (d, 1H), 2.6 (s, 3H), 1.6 (s, 9H)2-123 Cl, H, Cl CH₃ NHCH₂-(2-SCH₃—C₆H₄) B 1.539 569.5 2-124 Cl, H, ClCH₃ NHCH₂CH₂SO₂CH₃ B 1.323 539.4 2-125 Cl, H, Cl CH₃NHCH₂-(2-SO₂CH₃—C₆H₄) B 1.435 601.5 2-126 Cl, Cl, Cl CH₃NH-(1,1-dioxo-thiethan-3-yl) B 1.389 571.9 2-127 Cl, Cl, Cl CH₃NHCH₂C(═O)—NHCH₂CF₃ B 1.439 606.8 2-128 Cl, Cl, Cl CH₃ NHCH₂-(2-pyridyl)B 1.251 558.8 2-129 Cl, H, Cl CH₃ NH-[(1R)-(2-pyridyl)eth-1-yl] B 1.233538.3 2-130 Cl, H, Cl CH₃ NH-[(1S)-(2-pyridyl)eth-1-yl] B 1.221 538.32-131 Cl, Cl, Cl CH₃ NHCH₂CF₃ B 1.500 549.7 2-132 Cl, Cl, Cl CH₃NHCH₂-(4-thiazolyl) B 1.426 564.9 2-133 Cl, Cl, Cl CH₃ NH-(3-thiethanyl)B 1.492 539.0 2-134 Cl, H, Cl CH₃ NHCH₂-(3-pyridazinyl) B 1.302 525.32-135 Cl, H, Cl CH₃ NHCH₂-(4-isoxazolyl) B 1.376 514.2 2-136 Cl, H, ClCH₃ NHCH₂-(5-thiazolyl) B 1.354 530.3 2-137 Cl, Cl, Cl SCH₃NHCH₂-(2-pyridyl) B 1.243 592.1 2-138 Cl, Cl, Cl SCH₃ NHCH₂CF₃ B 1.500581.1 2-139 Cl, Cl, Cl SCH₃ NH-(1,1-dioxo-thiethan-3-yl) B 1.403 605.12-140 Cl, Cl, Cl SCH₃ NHCH₂C(═O)—NHCH₂CF₃ B 1.434 640.0 2-141 Cl, Cl, ClSCH₃ NHCH₂-(4-thiazolyl) B 1.442 598.0 2-142 Cl, Cl, Cl SCH₃NHCH₂-(2-thiazolyl) B 1.444 598.0 2-143 Cl, Cl, Cl CH₃NHCH₂-(2-thiazolyl) B 1.449 566.1 2-144 Cl, H, Cl CH₃ NHCH(CH₃)C(═O)— B1.402 586.2 NHCH₂CF₃ 2-145 Cl, H, Cl CH₃ NHCH₂C(═O)—NHCH₂CH₃ B 1.326518.2 2-146 Cl, H, Cl CH₃ NHCH₂C(═O)— B 1.362 532.2 NHCH(CH₃)₂ 2-147 Cl,H, Cl CH₃ NHCH₂C(═O)—NHCH₃ B 1.281 504.2 2-148 Cl, H, Cl CH₃ NHCH₂C(═O)—B 1.355 532.3 NHCH₂CH₂CH₃ 2-149 Cl, H, Cl CH₃ NHCH₂-(1,3-dioxolan-2-yl)B 1.368 519.2 2-150 Cl, Cl, Cl Cl NHCH₂-(2-pyridyl) B 1.245 580.1 2-151Cl, Cl, Cl Cl NHCH₂-(2-pyrimidyl) B 1.433 581.1 2-152 Cl, Cl, Cl ClNHCH₂-(2-thiazolyl) B 1.450 586.1 2-153 Cl, Cl, Cl ClNHCH₂C(═O)—NHCH₂CF₃ B 1.440 628.1 2-154 Cl, Cl, Cl Cl NHCH₂CF₃ B 1.508571.1 2-155 Cl, Cl, Cl Cl NH-(1,1-dioxo-thiethan-3-yl) 1H NMR (400 MHz,CDCl₃): δ 7.8 (s, 1H), 7.8-7.6 (m, 2H), 7.4 (s, 2H), 7.1 (d, 1H),5.0-4.8 (m, 1H), 4.7-4.6 (m, 2H), 4.2 (d, 1H), 4.2-4.0 (m, 2H), 3.9 (d,1H) 2-156 Cl, H, Cl CH₃ OH B 1.419 434.1 2-157 Cl, Cl, Cl CH₃ OH B 1.472470.1 2-158 Cl, Cl, Cl SCH₃ OH B 1.466 500.1 2-159 Cl, Cl, Cl Cl OH B1.477 490.0 2-160 Cl, F, Cl CH₃ OC(CH₃)₃ B 1.678 508.2 2-161 Cl, F, ClCH₃ OH B 1.417 454.0 2-162 Cl, F, Cl CH₃ NHCH₂C(═O)—NHCH₂CF₃ B 1.373590.2 2-163 Cl, F, Cl CH₃ NH-(1,1-dioxo-thiethan-3-yl) B 1.344 555.22-164 Cl, F, Cl CH₃ NHCH₂-(2-pyridyl) B 1.190 542.3 2-165 Cl, F, Cl CH₃NHCH₂CF₃ B 1.451 533.3 2-166 Cl, F, Cl CH₃ NHCH₂-(2-thiazolyl) B 1.391548.1 2-167 Cl, Cl, Cl OCH₃ OC(CH₃)₃ B 1.651 542.2 2-168 Cl, Cl, Cl OCH₃OH B 1.424 484.2 2-169 Cl, Cl, Cl OCH₃ NHCH₂C(═O)—NHCH₂CF₃ B 1.434 624.12-170 Cl, Cl, Cl OCH₃ NH-(1,1-dioxo-thiethan-3-yl) B 1.410 589.1 2-171Cl, Cl, Cl OCH₃ NHCH₂-(2-pyridyl) B 1.245 574.1 2-172 Cl, Cl, Cl OCH₃NHCH₂-(2-thiazolyl) B 1.469 580.1 2-173 Cl, Cl, Cl OCH₃ NHCH₂CH₂CF₃ B1.537 579.1 2-174 Cl, H, CF₃ CH₃ OC(CH₃)₃ B 1.657 524.3 2-175 Cl, Cl, ClH OC(CH₃)₃ B 1.687 512.1 2-176 Cl, H, CF₃ CH₃ OH B 1.413 468.2 2-177 Cl,Cl, Cl H OH B 1.435 456.1 2-178 Cl, H, Cl CH₃ NHNH-(2-pyridyl) B 1.153525.2 2-179 Cl, H, Cl CH₃ NHN(CH₃)-(2-pyridyl) B 1.201 539.2 2-180 Cl,H, Cl CH₃ NHCH₂CH₂CH₂CH₃ B 1.480 489.2 2-181 Cl, H, CF₃ CH₃NHCH₂C(═O)—NHCH₂CF₃ B 1.358 606.3 2-182 Cl, H, CF₃ CH₃ NHCH₂-(2-pyridyl)B 1.185 558.4 2-183 Cl, H, CF₃ CH₃ NH-(1,1-dioxo-thiethan-3-yl) B 1.343571.2 2-184 Cl, H, CF₃ CH₃ NHCH₂-(2-thiazolyl) B 1.384 564.2 2-185 Cl,H, CF₃ CH₃ NHCH₂CH₂CF₃ B 1.450 563.2 2-186 Cl, Cl, Cl HNHCH₂C(═O)—NHCH₂CF₃ B 1.393 594.2 2-187 Cl, Cl, Cl HNH-(1,1-dioxo-thiethan-3-yl) 1H NMR (400 MHz, CDCl₃): δ 8.1-7.7 (m, 4H),7.4 (s, 2H), 6.9- 6.8 (m, 1H), 5.0-4.8 (m, 1H), 4.8-4.6 (m, 2H), 4.2 (d,1H), 4.2-4.0 (m, 2H), 3.9 (d, 1H) 2-188 Cl, Cl, Cl H NHCH₂-(2-pyridyl) B1.211 544.1 2-189 Cl, Cl, Cl H NHCH₂-(2-thiazolyl) B 1.409 552.1 2-190Cl, Cl, Cl H NHCH₂CH₂CF₃ B 1.470 550.3 2-191 Cl, H, Cl CH₃NHCH₂-(6-CF₃-pyrid-2-yl) B 1.310 592.3 2-192 Cl, H, Cl CH₃NHNHC(═O)—NHCH₂CF₃ B 1.317 573.3 2-193 Cl, H, Cl CH₃ NH-(2- B 1.335517.2 oxotetrahydrofuran-3-yl) 2-194 Cl, H, Cl CH₃ OCH₂-(2-pyridyl) B1.420 525.3 2-195 Cl, H, Cl CH₃ NH-[2-oxo-1-(2,2,2- B 1.388 598.2trifluoroethyl)pyrrolidin-3-yl] 2-196 Cl, H, Cl CH₃ OCH₂CH₂CF₃ B 1.593530.2 2-197 Cl, H, Cl CH₃ NH-(2-pyrazinyl) B 1.421 511.2 2-198 Cl, H, ClCH₃ NH₂ B 1.310 433.2 2-199 Cl, H, Cl CH₃ NHCH═NOCH₃ B 1.459 490.3 2-200Cl, H, Cl CH₃ NH-(1-acetylazetidin-3-yl) B 1.284 530.3 2-201 Cl, H, ClCH₃ NH-(1-methyl-2-oxo- B 1.296 530.3 pyrrolidin-3-yl) 2-202 Cl, H, ClCH₃ NHCH₂CH₂OH A 3.705 477.0 2-203 Cl, H, Cl CH₃ NHCH₂CH₂OCH₂CH₃ A 4.141505.0 2-204 Cl, H, Cl CH₃ NHCH₂CH₂OCH₂CF₃ A 4.277 559.0 2-205 Cl, H, ClCH₃ NH2 B 1.398 434.2 2-206 Cl, H, Cl CH₃ NHCH₂CH₂OCH₃ B 1.353 491.42-207 Cl, H, Cl CH₃ NHCH(CH₃)CH₂OCH₃ B 1.393 505.3 2-208 Cl, H, Cl CH₃NHCH₂CH₂CH₂CF₃ B 1.459 543.0 2-209 Cl, H, Cl CH₃ NHCH₂CF₂CF₃ B 1.494565.2 2-210 Cl, H, Cl CH₃ NHCH₂CH₂SCF₃ B 1.487 561.4 2-211 Cl, H, Cl CH₃NHCH₂CH₂OCF₃ B 1.447 545.3 2-212 Cl, H, Cl CH₃ N(CH₃)—CH₂C(═O)— B 1.377586.4 NHCH₂CF₃ 2-213 Cl, H, Cl SCH₃ NHCH₂CF₃ B 1.444 547.1 2-214 Cl, H,Cl SCH₃ pyrrolidin-1-yl B 1.463 519.2 2-215 Cl, H, Cl SCH₃NHCH₂-(2-pyridyl) B 1.200 556.2 2-216 Cl, H, Cl SCH₃ NHCH₂C(═O)—NHCH₂CF₃B 1.369 604.2 2-217 Cl, H, Cl SCH₃ NHCH₂-(2-pyrimidyl) B 1.346 557.22-218 Cl, H, Cl SCH₃ NHCH₂-(2-thiazolyl) B 1.371 564.0 2-219 Cl, H, ClSCH₃ NH-(1,1-dioxo-thiethan-3-yl) B 1.331 569.2 2-220 Cl, H, Cl SCH₃NH-(3-thiethanyl) B 1.425 538.9 2-221 Cl, H, Cl CH₃ NHCH₂C(═O)— B 1.319528.4 NHCH₂CCH 2-222 Cl, H, Cl CH₃ NHCH₂C(═O)—N(CH₃)— B 1.402 586.4CH₂CF₃ 2-223 Cl, H, Cl CH₃ NH-(4-CF₃-thiazol-2-yl) B 1.407 584.4 2-224Cl, Cl, Cl CH₃ NHCH₂-(2-pyrimidyl) B 1.397 561.1 2-225 Cl, F, Cl CH₃NHCH₂-(2-pyrimidyl) B 1.340 543.2 2-226 Cl, H, Cl CH₃NHCH₂-(5-Cl-pyrid-2-yl) B 1.400 560.1 2-227 Cl, H, CF₃ CH₃NHCH₂-(2-pyrimidyl) B 1.382 559.2 2-228 Cl, H, Cl CH₃ NHNH-(2-pyrimidyl)B 1.341 526.2 2-229 Cl, H, Cl CH₃ NH-(5-pyrimidyl) B 1.382 511.0 2-230Cl, H, Cl CH₃ NH-(2-pyrimidyl) B 1.349 511.0 2-231 Cl, H, Cl CH₃NHCH═NOCH₂CF₃ B 1.527 557.9 2-232 Cl, H, Cl CH₃ NHNHC(═O)— B 1.318 555.4NHCH₂CHF₂ 2-233 Cl, H, Cl CH₃ NHCH₂C(═O)—NHCH₂CN B 1.300 529.3 2-234 Cl,H, Cl CH₃ NH-(3-oxo-isoxazolidin-4-yl) B 1.282 519.9

C.3 Compound Examples 3

Compound examples 3-1 to 3-28 correspond to compounds of formula C.3:

wherein R^(2a), R^(2b), R^(2c), R⁴, R⁵ and R⁶ of each synthesizedcompound is defined in one row of table C.3 below.

The compounds were synthesized in analogy to Synthesis Example S.3.

TABLE C.3 R^(2a), HPLC-MS: R^(2b), Method, R_(t) (min) Ex. R^(2c) R⁴ R⁵R⁶ and [M + H]⁺ 3-1 Cl, H, CH₃ H C(═O)CH₂SCH₂CH₃ B 1.503 521.1 Cl 3-2Cl, H, CH₃ C₂H₅ H B 1.142 447.3 Cl 3-3 Cl, H, CH₃ C₂H₅ C(═O)CH₂SCH₂CH₃ A4.639 549.0 Cl 3-4 Cl, H, CH₃ C₂H₅ C(═O)-(cyclopropyl) A 4.547 515.0 Cl3-5 Cl, H, CH₃ C₂H₅ C(═O)CH₂SO₂CH₃ A 4.214 567.0 Cl 3-6 Cl, H, Cl H H B1.085 440.8 Cl 3-7 Cl, H, Cl H C(═O)CH₂SCH₂CH₃ B 1.511 542.9 Cl 3-8 Cl,H, Cl H C(═O)CH₂SO₂CH₃ B 1.376 560.9 Cl 3-9 Cl, H, Cl H C(═O)(cyclopropyl) B 1.461 508.9 Cl 3-10 Cl, H, Cl C₂H₅ C(═O)CH₂CF₃ B 1.555579.2 Cl 3-11 Cl, H, Cl C₂H₅ C(═O)CH₃ B 1.513 511.1 Cl 3-12 Cl, H, ClC₂H₅ C(═O)C₂H₅ B 1.560 525.1 Cl 3-13 Cl, H, Cl C₂H₅ C(═O)-pyrid-3-yl B1.395 574.1 Cl 3-14 Cl, H, Cl C₂H₅ C(═O)-pyrid-2-yl B 1.534 574.1 Cl3-15 Cl, H, Cl C₂H₅ C(═O)-2,3- B 1.601 609.2 Cl difluorophenyl 3-16 Cl,H, Cl C₂H₅ C(═O)C₆H₅ B 1.598 573.1 Cl 3-17 Cl, H, Cl C₂H₅C(═O)-(cyclopropyl) B 1.566 537.1 Cl 3-18 Cl, H, Cl C₂H₅ C(═O)CH₂SO₂CH₃B 1.455 589.1 Cl 3-19 Cl, H, Cl C₂H₅ C(═O)CH₂SCH₂CH₃ B 1.596 571.0 Cl3-20 Cl, H, Cl C₂H₅ C(═O)CH₂SCF₃ B 1.603 611.0 Cl 3-21 Cl, H, Cl HC(═O)C₂H₅ B 1.430 497.2 Cl 3-22 Cl, H, Cl H C(═O)NHCH₂CF₃ B 1.424 566.2Cl 3-23 Cl, H, Cl H C(═O)CH₃ B 1.379 481.1 Cl 3-24 Cl, H, Cl HC(═O)CH₂CF₃ B 1.462 551.2 Cl 3-25 Cl, H, Cl C₂H₅ C(═O)CH(CH₃)₂ B 1.591537.2 Cl 3-26 Cl, H, Cl H C(═O)NHCH₂CH₃ B 1.399 512.1 Cl 3-27 Cl, H, ClH C(═O)CH(CH₃)₂ B 1.497 509.2 Cl 3-28 Cl, H, Cl C₂H₅ C(═O)-(1,1- B 1.495601.2 Cl dioxothietan-3-yl)

C.4 Compound Examples 4

Compound example 4-1 corresponds to compounds of formula C.4:

wherein R^(2a), R^(2b), R^(2c), R⁴, and A⁴ of each synthesized compoundis defined in one row of table C.4 below.

Compound 4-1 was synthesized in analogy to Synthesis Example S.2. Thestarting material(2-(1,2,4-triazol-1-yl)-5-[(Z)-4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-2-enoyl]benzonitrile)was prepared in analogy to the method described in EP-A-2172462.

TABLE C.4 HPLC-MS: Method, R_(t) (min) Ex. R^(2a), R^(2b), R^(2c) —R⁴ A⁴and [M + H]⁺ 4-1 Cl, Cl, Cl —CN 1,2,4-triazol-1-yl B 1.463 504.1

C.5 Compound Examples 5

Compound examples 5-1 to 5-15 correspond to compounds of formula C.5:

wherein R^(2a), R^(2b), R^(2c), R^(3a), G¹, R^(4a), R^(4b), and Y ofeach synthesized compound is defined in one row of table C.5 below.

Compounds 5-1 to 5-3 were synthesized in analogy to Synthesis ExampleS.4.

Compounds 5-4 to 5-15 were synthesized in analogy to Synthesis ExampleS.2.

TABLE C.5 HPLC-MS: Method, R_(t) (min) & [M + H]⁺ Ex. R^(2a), R^(2b),R^(2c) R^(3a) G¹ R^(4a) R^(4b) Y or ¹H-NMR 5-1 Cl, H, Cl F CH H CH₃NHCH₂C(═O)—NHCH₂CF₃ B 1.364 590.2 5-2 Cl, H, Cl F CH H CH₃NHCH₂-(2-pyridyl) B 1.192 543.9 5-3 Cl, H, Cl F CH H CH₃NH-(1,1-dioxo-thiethan-3-yl) 1H NMR (400 MHz, CDCl₃): δ 7.8-7.7 (m, 2H),7.5-7.4 (m, 2H), 7.3 (s, 2H), 6.5 (d, 1H), 6.3 (d, 1H, CHF), 5.0-4.8 (m,1H), 4.7- 4.5 (m, 2H), 4.1-3.9 (m, 2H), 2.5 (s, 3H) 5-4 Cl, Cl, Cl H N HCH₃ NHCH₂C(═O)—NHCH₂CF₃ B 1.432 608.8 5-5 Cl, Cl, Cl H N H CH₃NHCH₂-(2-pyridyl) B 1.254 559.2 5-6 Cl, Cl, Cl H N H CH₃NHCH₂-(2-pyrimidyl) B 1.396 561.8 5-7 Cl, Cl, Cl H N H CH₃NH-(1,1-dioxo-thiethan-3-yl) B 1.376 573.7 5-8 Cl, Cl, Cl H N H CH₃NHCH₂CH₂CF₃ B 1.504 563.9 5-9 Cl, Cl, Cl H CCH₃ CH₃ H OCH₃ 1H NMR (400MHz, CDCl₃): δ 7.7 (s, 2H), 7.4 (s, 2H), 4.0 (d, 1H), 3.9 (s, 3H), 3.6(d, 1H), 2.3 (s, 6H) 5-10 Cl, Cl, Cl H CCH₃ CH₃ H NHCH₂C(═O)—NHCH₂CF₃ B1.445 621.8 5-11 Cl, Cl, Cl H CCH₃ CH₃ H NHCH₂-(2-pyridyl) B 1.256 574.15-12 Cl, Cl, Cl H CCH₃ CH₃ H NHCH₂CF₃ B 1.512 564.9 5-13 Cl, Cl, Cl HCCH₃ CH₃ H NHCH₂-(2-thiazolyl) B 1.447 579.8 5-14 Cl, Cl, Cl H CCH₃ CH₃H NHCH₂-(2-pyrimidyl) B 1.415 574.8 5-15 Cl, Cl, Cl H CCH₃ CH₃ HNH-(1,1-dioxo-thiethan-3-yl) B 1.436 585.1

C.6 Compound Examples 6 Intermediates

Intermediates 6-1 to 6-7 correspond to compounds of formula C.6:

wherein R^(2a), R^(2b), R^(2c), R⁴, and YY of each synthesized compoundis defined in one row of table C.6 below.

HPLC-MS: Method, R_(t) (min) & [M + H]⁺ Ex. R^(2a), R^(2b), R^(2c) R⁴ YYor 1H-NMR 6-1 Cl, H, Cl CH₃ Br 1H NMR (400 MHz, CDCl₃): δ 7.7-7.5 (m,2H), 7.5- 7.3 (m, 2H), 7.3 (s, 2H), 4.2 (d, 1H), 3.8 (d, 1H), 2.4 (s,3H) 6-2 Cl, H, Cl Cl Br B 1.676 489.8 6-3 Cl, H, Cl F Br 1H NMR (400MHz, CDCl₃): δ 7.7-7.5 (m, 2H), 7.5- 7.3 (m, 2H), 7.3 (s, 2H), 4.2 (d,1H), 3.8 (d, 1H) 6-4 Cl, H, Cl Cl CH₂OH 1H NMR (400 MHz, CDCl₃): δ 7.8(s, 1H), 7.7-7.5 (m, 2H), 7.4 (s, 1H), 7.3, (s, 2H), 4.8 (s, 2H), 4.2(d, 1H), 3.8 (d, 1H), 1.7 (br. s, 1H) 6-5 Cl, Cl, Cl OCH₃ CH₂OH 1H NMR(400 MHz, CDCl₃): δ 7.5-7.4 (m, 3H), 7.3 (d, 1H), 7.2 (d, 1H), 4.7 (s,2H), 4.2 (d, 1H), 3.9 (s, 3H), 3.8 (d, 1H) 6-6 Cl, H, Cl Cl CH₂N₃ 1H NMR(400 MHz, CDCl₃): δ 7.8 (s, 1 H), 7.7 (d, 1H), 7.5 (d, 1H), 7.4 (s, 1H),7.3, (s, 2H), 4.5 (s, 2H), 4.2 (d, 1H), 3.8 (d, 1H) 6-7 Cl, H, Cl CH₃CH₂OH 1H NMR (400 MHz, CDCl₃): δ 7.7-7.5 (m, 2H), 7.5 (d, 1H), 7.4 (s,1H), 7.3, (s, 2H), 4.7 (s, 2H), 4.2 (d, 1H), 3.8 (d, 1H), 2.4 (s, 3H),1.7 (br. s, 1H)

Synthesis Example S.11-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-phenyl]methyleneamino]-3-ethyl-urea

(Compound example 1-5; compound of formula IA, wherein R^(2a) and R^(2c)are Cl, R² is H, R⁴ is methyl and A is A¹=—CH(═N—NH—C(═O)—NH—CH₂CH₃).

Step 1:1-(4-Bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-3-sulfanyl-butan-1-one

1-(4-Bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)but-2-en-1-one (21.5g, 4:1-mixture of E/Z-isomers) in CH₂Cl₂ (400 mL) was treated withtriethylamine (68 mL). At 0° C., gaseous hydrogen sulfide (H₂S) wasbubbled through the solution for 10 min. The mixture was stirred foranother 20 min at 0° C., and then diluted with CH₂Cl₂ (300 mL). Theorganic layer was washed with 6% aqueous hydrochloric acid (300 mL),dried (MgSO₄), filtered, and concentrated.

The product was obtained as a yellowish oil (23.1 g, 99.7%).

HPLC-MS (method B): 1.557 min, M=472.90.

Step 2:3-(4-Bromo-3-methyl-phenyl)-5-(3,5-dichlorophenyl)-5-methyl-4H-isothiazole

At −15° C., the product of step 1 (23 g) in CH₂Cl₂ (400 mL) was treatedwith triethylamine (27.1 mL) and with a solution ofhydroxylamine-O-sulfonic acid (“HOSA”, 6.23 g) in water (10 mL). Thereaction was warmed to 0° C. and stirred at 0° C. for 45 min, and thendiluted with CH₂Cl₂ (400 mL). The organic layer was washed withsaturated aqueous NH₄Cl solution (3×), dried (MgSO₄), and filtered. Tothe obtained solution, acid washed molecular sieves (AW 300, 150 g) wereadded and the mixture was stirred vigorously for 90 min at roomtemperature. Then, the molecular sieves were filtered off, and thefiltrate concentrated to afford a residue that was purified by flashchromatography on silica gel (ethyl acetate/cyclohexane). The obtainedpale yellow solid (19.5 g) was titurated with hexanes (3×) to afford theproduct as a white solid (15.6 g, 68%).

HPLC-MS (method B): 1.697 min, M=469.90.

Step 3: Methyl4-[5-(3,5-dichlorophenyl)-5-methyl-4H-isothiazol-3-yl]-2-methyl-benzoate

The product of step 2 (14.6 g) in methanol/THF (63 mL/6 mL) was treatedwith [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)(“Pd(dppf)Cl₂”, 5.08 g), Pd(OAc)₂ (0.42 g), NaOAc (3.7 g). The reactionwas subsequently pressurized twice with N₂ (3.5 bar) and three timeswith carbon monoxide (5 bar). Then, the mixture was pressurized withcarbon monoxide (7.5 bar) and heated at 80° C. (internal temperature)for 13 h. Thereby, the carbon monoxide pressure was adjusted severaltimes back to 7.5 bar. Then, the reaction was cooled to roomtemperature, filtered over celite (CH₂Cl₂) and subsequently filteredover a plug of silica gel. The product was obtained as a pale yellowfoam (13.1 g, 89%).

HPLC-MS (method A): 3.974 min, M=566.00.

Step 4:[4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-phenyl]methanol

To a solution of the product of step 3 (4.9 g) in CH₂Cl₂ (100 mL) at 0°C. was added a solution of DIBAL-H in toluene (1.5 M, 16 mL). Theresulting solution was stirred at 0° C. for 90 min and quenched byadding MeOH (10 mL). A saturated solution of Rochelle's salt (potassiumsodium tartrate, CAS 304-59-6) (100 mL) was added, followed by vigorousstirring at r.t. for 2 h. Then, CH₂Cl₂ (300 mL) was added, and theorganic layer was washed with water, dried (Na₂SO₄), filtered, andconcentrated to afford a residue that was purified by flashchromatography on silica gel (ethyl acetate/hexanes).

The product was obtained as pale yellow solid (3.45 g, 75%).

HPLC-MS (methode A): 4.390 min, M=419.95.

Step 5:4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methylbenzaldehyde

To a solution of the product of step 1 (1 g) in CH₂Cl₂ (40 mL) at r.t.was added DessMartin-Periodane (CAS 87413-09-0) (1.11 g). The reactionwas stirred overnight, filtered and concentrated. The residue waspurified by flash chromatography on silica gel (ethylacetate/cyclohexane). The product was obtained as a viscous oil (0.81 g,81%).

HPLC-MS (method A): 4.036 min, M=417.90.

Step 6:1-[(E)-[4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-phenyl]methyleneamino]-3-ethyl-urea

A solution of the product of step 2 (0.15 g) and 1-ammonium-3-ethyl ureahydrochloride (60 mg) in EtOH (4 mL) and acetic acid (0.14 mL) wasstirred at 70° C. overnight, and concentrated. The residue was purifiedby flash chromatography on silica gel (ethyl acetate/cyclohexane). Theproduct was obtained as a pale yellow foam (0.10 g, 55%).

HPLC-MS (method B): 1.484 min, M=505.0.

Synthesis Example S.24-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4H-isothiazol-3-yl]-2-methyl-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]benzamide

(Compound example 2-1; compound of formula IA, wherein R^(2a) and R^(2c)are Cl, R² is H, R⁴ is methyl and A is A²=—C(═O)—NH—CH₂—C(═O)—NH—CH₂CF₃)

Step 1:4-[5-(3,5-dichlorophenyl)-5-methyl-4H-isothiazol-3-yl]-2-methyl-benzoicacid

To a solution of methyl4-[5-(3,5-dichlorophenyl)-5-methyl-4H-isothiazol-3-yl]-2-methyl-benzoate(=the product of step 3 of example 1) (2.4 g) in THF (50 mL) was added asolution of LiOH (0.51 g) in water (50 mL). The reaction was stirred for16 h at room temperature, then diluted with water (300 mL) and washedwith CH₂Cl₂ (3×). The aqueous phase was acidified with aqueous 1 M HClto pH 1-2 and extracted with CH₂Cl₂ (3×). The combined organic layerswere washed with water, dried (Na₂SO₄), filtered, and concentrated. Theproduct was obtained as a pale yellow solid (2.24 g, 96%).

HPLC-MS (method A): 4.458 min, M=433.95.

Step 2:4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4H-isothiazol-3-yl]-2-methyl-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]benzamide

To a solution of the product of step 1 (2.2 g),[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]ammonium chloride (1.22 g) andbromotripyrrolidinophosphonium hexafluorophosphate (“PyBroP”, 2.95 g) inCH₂Cl₂ (100 mL) at room temperature was added N,N-diisopropylethylamine(3.53 mL). The reaction was stirred at room temperature for 16 h, thenconcentrated and redissolved in ethyl acetate (200 mL). The organiclayer was washed with 5% aqueous HCl (2×) and 5% aqueous K₂CO₃ (2×),dried (Na₂SO₄), filtered, and concentrated to afford a residue that waspurified by flash chromatography on silica gel (ethylacetate/cyclohexane). The product was obtained as amorphous white foam(2.45 g, 84%).

HPLC-MS (method A): 4.045 min, M=572.00.

Synthesis Example S.3N-[[4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-phenyl]methyl]-N-ethyl-2-ethylsulfanyl-acetamide

(Compound example 3-3; compound of formula IA, wherein R^(2a) and R^(2c)are Cl, R² is H, R⁴ is methyl and A isA³=—CH₂—N(CH₂CH₃)—C(═O)—CH₂SCH₂CH₃).

Step 1:N—[[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-phenyl]methyl]ethanamine

To a solution of[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-phenyl]methanol(i.e. the product of example 1, step 4) (1.5 g) in CH₂Cl₂ (50 mL) wasadded triethylamine (0.75 mL) and methansulfonylchloride (0.63 g) atr.t. The reaction was stirred at r.t. overnight, then diluted with ethylacetate (200 mL), and washed with water (3×), dried (Na₂SO₄), filtered,and concentrated to afford the crude mesylate (1.19 g) that wasre-dissolved in acetonitrile (30 mL) and treated with a solution ofethylamine in THF (2 M, 8.8 mL). The reaction was stirred overnight atr.t. The residue was taken up in ethyl acetate and washed with 5%aqueous potassium carbonate solution (3×), dried (Na₂SO₄), filtered, andconcentrated to afford the product as a solid (0.98 g, 59%).

HPLC-MS (method B): 1.139 min, M=447.3.

Step 2:N—[[4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-phenyl]methyl]-N-ethyl-2-ethylsulfanyl-acetamide

To a solution of the product of step 1 (0.30 g), (ethylthio)acetic acid(0.10 g) and bromotripyrrolidinophosphonium hexafluorophosphate(“PyBroP”, 0.39 g) in CH₂Cl₂ (20 mL) at r.t. was addedN,N-diisopropylethylamine (0.47 mL). The reaction was stirred at r.t.for 16 h, then concentrated to afford a residue that was purified byflash chromatography on silica gel (ethyl acetate/cyclohexane). Theproduct was obtained as amorphous foam (330 mg, 90%).

HPLC-MS (method A): 4.639 min, M=549.00.

Synthesis Example S.44-[5-(3,5-dichlorophenyl)-4-fluoro-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]benzamide

(Compound example 5-1; compound of formula C.5, wherein R^(2a) andR^(2c) are Cl, R^(2b) is H, R^(3a) is F, G is CH, R^(4a) is H, R^(4b) ismethyl and Y is —NHCH₂—C(═O)—NHCH₂CF₃).

Step 1: tert-butyl4-[5-(3,5-dichlorophenyl)-4-fluoro-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoate

To a solution of [tert-butyl4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoate(prepared from “tert-butyl4-[(Z)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-but-2-enoyl]-2-methyl-benzoate”in analogy to Synthesis Example S.1, step 1 and step 2) (2.55 g) in THF(40 mL) under nitrogen at −78° C. was added LiHMDS (5.7 mL, 1M solutionin THF) and the mixture was stirred for 1.5 h at −78° C. Then,N-fluorobenzenesulfonimide (“NFSI”, 2.1 g) was added at −78° C. in oneportion and the mixture was stirred at −78° C. for another 2 h. Then,the reaction was quenched with saturated aqueous NH₄Cl solution. EtOAcwas added and the organic layer was washed with water (3×), dried(Na₂SO₄), filtered, and concentrated to afford a residue that waspurified by flash chromatography on silica gel (ethylacetate/cyclohexane). The product was obtained as yellow oil (1.65 g,62%).

1H NMR (400 MHz, CDCl₃, signals of major diastereomer): δ 7.9 (d, 1H),7.7-7.6 (m, 2H), 7.5 (s, 1H), 7.4 (s, 2H), 6.4 (d, 1H, CHF), 2.6 (s,3H), 1.6 (s, 9H).

Step 2:4-[5-(3,5-dichlorophenyl)-4-fluoro-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoicacid

To a solution of the product of step 1 (0.36 g) in CH₂Cl₂ (20 mL) at 0°C. was added trifluoroacetic acid (“TFA”, 10 mL), and the mixture wasstirred at r.t. overnight. Then, the reaction was concentrated,azeotroped with CH₂Cl₂ (5×) and triturated with petroleum ether/EtOAc(40:1) to obtain the product as a pale yellow solid (0.28 g, 87%).

1H NMR (400 MHz, d6-DMSO, signals of major diastereomer): δ 8.0-7.8 (m,4H), 7.7 (s, 2H), 7.5 (d, 1H, CHF), 2.6 (s, 3H).

Step 3:4-[5-(3,5-dichlorophenyl)-4-fluoro-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]benzamide

To a solution of the product of step 2 (0.25 g) in toluene/CH₂Cl₂ (1:1,20 mL) was added N,N-dimethylformamide (“DMF”, 1 drop) and oxalylchloride (0.14 mL). The reaction was stirred overnight, concentrated,and azeotroped with CH₂Cl₂ (5×). The obtained residue (0.26 g) wasdissolved in THF (30 mL) and added to a solution of2-amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride andtriethylamine (0.22 g) in THF (30 mL). The reaction was stirredovernight, filtered and concentrated to afford a residue that waspurified by flash chromatography on silica gel (ethylacetate/cyclohexane). The product was obtained as amorphous foam (0.13g, 40%).

HPLC-MS (method B): 1.364 min, M=590.2.

II. Evaluation of Pesticidal Activity:

The activity of the compounds of formula I of the present invention canbe demonstrated and evaluated by the following biological test.

B.1 Cotton Aphid (Aphis gossypii)

The active compounds were formulated in cyclohexanone as a 10,000 ppmsolution supplied in tubes. The tubes were inserted into an automatedelectrostatic sprayer equipped with an atomizing nozzle and they servedas stock solutions for which lower dilutions were made in 50%acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was includedin the solution at a volume of 0.01% (v/v).

Cotton plants at the cotyledon stage were infested with aphids prior totreatment by placing a heavily infested leaf from the main aphid colonyon top of each cotyledon.

Aphids were allowed to transfer overnight to accomplish an infestationof 80-100 aphids per plant and the host leaf was removed. The infestedplants were then sprayed by an automated electrostatic plant sprayerequipped with an atomizing spray nozzle. The plants were dried in thesprayer fume hood, removed from the sprayer, and then maintained in agrowth room under fluorescent lighting in a 24-hr photoperiod at 25° C.and 20-40% relative humidity. Aphid mortality on the treated plants,relative to mortality on untreated control plants, was determined after5 days.

In this test, the compounds 2-4, 2-10, 2-12, 2-15, 2-19, 2-26, 2-27,2-28, 2-29, 2-31, 2-32, 2-35, 2-37, 2-38, 2-42, 2-43, 2-47, 2-48, 2-49,2-50, 2-53, 2-57, 2-59, 2-62, 2-63, 2-65, 2-68, 2-71, 2-72, 2-73, 2-74,2-75, 2-82, 2-83, 2-86, 2-88, 2-93, 2-99, 2-109, 2-118, 2-137, 2-138,2-142, 2-143, 2-145, 2-149, 2-150, 2-151, 2-152, 2-153, 2-162, 2-163,2-164, 2-166, 2-171, 2-178, 2-182, 2-183, 2-185, 2-195, 2-199, 3-11, and3-12 at 100 ppm, respectively, showed a mortality of at least 75% incomparison with untreated controls.

B.2 Cowpea Aphid (Aphis craccivora)

Potted cowpea plants colonized with approximately 100-150 aphids ofvarious stages were sprayed after the pest population had been recorded.Population reduction was assessed after 24, 72, and 120 hours.

In this test, the compounds 1-13, 2-1, 2-2, 2-4, 2-8, 2-9, 2-10, 2-11,2-12, 2-15, 2-19, 2-26, 2-28, 2-32, 2-33, 2-34, 2-35, 2-36, 2-38, 2-47,2-51, 2-54, 2-55, 2-59, 2-69, 2-137, 2-142, 2-150, 2-151, 2-152, 2-162,2-164, 2-165, 2-166, 2-178, 2-180, 2-181, 2-182, 2-184, 2-185, 2-197,2-199, 2-200, 2-215, 2-217, 2-218, 2-220, 2-223, 2-224, 2-225, 2-227,3-1, 3-2, 3-8, 3-9, 3-11, 3-12, 3-21, 3-23, 4-1, and 5-2 at 500 ppm,respectively, showed a mortality of at least 75% in comparison withuntreated controls.

B.3 Diamond Back Moth (Plutella xylostella)

Leaves of Chinese cabbage were dipped in test solution and air-dried.Treated leaves were placed in petri dished lined with moist filterpaper. Mortality was recorded 24, 72, and 120 hours after treatment.

In this test, the compounds 1-1, 1-2, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9,1-10, 1-11, 1-12, 1-13, 1-15, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8,2-9, 2-10, 2-11, 2-12, 2-13, 2-15, 2-18, 2-19, 2-20, 2-21, 2-22, 2-23,2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-34, 2-35, 2-36, 2-37,2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49,2-50, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61,2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73,2-74, 2-75, 2-76, 2-77, 2-78, 2-80, 2-81, 2-82, 2-83, 2-84, 2-85, 2-86,2-87, 2-88, 2-89, 2-90, 2-91, 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98,2-99, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108,2-109, 2-111, 2-112, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120,2-121, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131,2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141,2-142, 2-143, 2-144, 2-145, 2-146, 2-147, 2-148, 2-149, 2-150, 2-151,2-152, 2-153, 2-154, 2-155, 2-162, 2-163, 2-164, 2-165, 2-166, 2-169,2-170, 2-171, 2-172, 2-173, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183,2-184, 2-185, 2-186, 2-188, 2-189, 2-190, 2-191, 2-192, 2-193, 2-194,2-195, 2-197, 2-198, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-206,2-207, 2-208, 2-209, 2-210, 2-211, 2-212, 2-213, 2-214, 2-215, 2-216,2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223, 2-224, 2-225, 2-226,2-227, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12,3-13, 3-14, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-25,3-26, 3-27, 4-1, 5-1, 5-2, 5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 500 ppm,respectively, showed a mortality of at least 75% in comparison withuntreated controls.

B.4 Green Peach Aphid (Myzus persicae)

For evaluating control of green peach aphid (Myzus persicae) throughsystemic means the test unit consisted of 96-well-microtiter platescontaining liquid artificial diet under an artificial membrane.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds werepipetted into the aphid diet, using a custom built pipetter, at tworeplications.

After application, 5-8 adult aphids were placed on the artificialmembrane inside the microtiter plate wells. The aphids were then allowedto suck on the treated aphid diet and incubated at about 23±1° C. andabout 50±5% relative humidity for 3 days. Aphid mortality and fecunditywas then visually assessed.

In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-7, 1-8, 1-9,1-10, 1-12, 1-13, 1-14, 1-15, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8,2-9, 2-10, 2-11, 2-12, 2-13, 2-15, 2-18, 2-19, 2-20, 2-21, 2-23, 2-24,2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-35, 2-37, 2-38, 2-39,2-40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-51, 2-52,2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64,2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73, 2-74, 2-75, 2-76,2-77, 2-81, 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91,2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101, 2-102,2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-110, 2-111, 2-112,2-113, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-123,2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133,2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143,2-145, 2-146, 2-147, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154,2-155, 2-159, 2-160, 2-162, 2-163, 2-164, 2-165, 2-166, 2-167, 2-168,2-169, 2-170, 2-171, 2-172, 2-173, 2-177, 2-178, 2-179, 2-180, 2-181,2-182, 2-183, 2-184, 2-185, 2-186, 2-187, 2-188, 2-189, 2-190, 2-191,2-192, 2-193, 2-194, 2-195, 2-196, 2-197, 2-199, 2-200, 2-201, 2-202,2-203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-211, 2-215, 2-216,2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223, 2-224, 2-225, 2-226,2-227, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-13, 3-14,3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-25, 3-26, 3-27,3-28, 4-1, 5-1, 5-2,5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 2500 ppm,respectively, showed a mortality of at least 75% in comparison withuntreated controls.

B.5 Mediterranean Fruitfly (Ceratitis capitata)

For evaluating control of Mediterranean fruitfly (Ceratitis capitata)the test unit consisted of microtiter plates containing an insect dietand 50-80 C. capitata eggs.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds weresprayed onto the insect diet at 5 μl, using a custom built microatomizer, at two replications.

After application, microtiter plates were incubated at about 28±1° C.and about 80±5% relative humidity for 5 days. Egg and larval mortalitywas then visually assessed.

In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9,1-10, 1-11, 1-12, 1-13, 1-14, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8,2-9, 2-10, 2-11, 2-12, 2-13, 2-15, 2-18, 2-19, 2-20, 2-21, 2-23, 2-26,2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-34, 2-35, 2-37, 2-38, 2-39,2-40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-51, 2-52,2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64,2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73, 2-74, 2-75, 2-76,2-77, 2-78, 2-80, 2-81, 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89,2-90, 2-91, 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100,2-101, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-111, 2-112,2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-123, 2-124,2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-135,2-138, 2-140, 2-141, 2-142, 2-143, 2-146, 2-147, 2-148, 2-149, 2-150,2-151, 2-152, 2-153, 2-154, 2-155, 2-162, 2-163, 2-164, 2-165, 2-166,2-169, 2-170, 2-171, 2-172, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183,2-184, 2-185, 2-186, 2-187, 2-188, 2-189, 2-190, 2-191, 2-192, 2-194,2-195, 2-197, 2-198, 2-199, 2-200, 2-201, 2-202, 2-203, 2-206, 2-207,2-209, 2-212, 2-215, 2-216, 2-217, 2-218, 2-220, 2-221, 2-222, 2-223,2-224, 2-225, 2-226, 2-227, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10,3-11, 3-12, 3-13, 3-14, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23,3-24, 3-25, 3-26, 3-27, 3-28, 4-1, 5-1, 5-2, 5-3, 5-4, and 5-7 at 2500ppm, respectively, showed a mortality of at least 75% in comparison withuntreated controls.

B.6 Orchid Thrips (Dichromothrips corbetti)

Dichromothrips corbetti adults used for bioassay were obtained from acolony maintained continuously under laboratory conditions. For testingpurposes, the test compound was diluted to a concentration of 500 ppm(wt compound: vol diluent) in a 1:1 mixture of acetone:water (vol:vol),plus 0.01% vol/vol Kinetic® surfactant.

Thrips potency of each compound was evaluated by using afloral-immersion technique. Plastic petri dishes were used as testarenas. All petals of individual, intact orchid flowers were dipped intotreatment solution and allowed to dry. Treated flowers were placed intoindividual petri dishes along with 10-15 adult thrips. The petri disheswere then covered with lids. All test arenas were held under continuouslight and a temperature of about 28° C. for duration of the assay. After4 days, the numbers of live thrips were counted on each flower, andalong inner walls of each petri dish. The level of thrips mortality wasextrapolated from pre-treatment thrips numbers.

In this test, the compounds 1-1, 1-2, 1-5, 1-7, 1-8, 1-9, 1-10, 1-132-1, 2-2, 2-3, 2-4, 2-5,2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13,2-15, 2-18, 2-19, 2-20, 2-21, 2-22, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30,2-31, 2-33, 2-34, 2-35, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-45,2-46, 2-47, 2-48, 2-49, 2-50, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57,2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69,2-70, 2-71, 2-72, 2-73, 2-74, 2-75, 2-76, 2-77, 2-78, 2-80, 2-81, 2-82,2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91, 2-92, 2-93, 2-94,2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105,2-106, 2-107, 2-108, 2-109, 2-111, 2-112, 2-113, 2-114, 2-115, 2-116,2-117, 2-118, 2-119, 2-120, 2-121, 2-123, 2-124, 2-125, 2-126, 2-127,2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137,2-138, 2-139, 2-140, 2-141, 2-142, 2-143, 2-144, 2-145, 2-146, 2-147,2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-162, 2-163,2-164, 2-165, 2-166, 2-169, 2-170, 2-171, 2-172, 2-173, 2-178, 2-179,2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-187, 2-188, 2-189,2-190, 2-192, 2-193, 2-195, 2-197, 2-198, 2-199, 2-200, 2-201, 2-202,2-203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-211, 2-212, 2-213,2-214, 2-215, 2-216, 2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223,2-224, 2-225, 2-226, 2-227, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9,3-10, 3-11, 3-12, 3-13, 3-14, 3-15, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21,3-22, 3-23, 3-24, 3-25, 3-26, 3-27, 4-1, 5-1, 5-2, 5-3, 5-4, 5-5, 5-6,5-7, and 5-8 at 500 ppm, respectively, showed a mortality of at least75% in comparison with untreated controls.

B.7 Rice Green Leafhopper (Nephotettix virescens)

Rice seedlings were cleaned and washed 24 hours before spraying. Theactive compounds were formulated in 50:50 acetone:water (vol:vol), and0.1% vol/vol surfactant (EL 620) was added. Potted rice seedlings weresprayed with 5 ml test solution, air dried, placed in cages andinoculated with 10 adults. Treated rice plants were kept at about 28-29°C. and relative humidity of about 50-60%. Percent mortality was recordedafter 72 hours.

In this test, the compounds 1-7, 2-1, 2-2, 2-4, 2-5, 2-6, 2-9, 2-10,2-11, 2-13, 2-15, 2-19, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32,2-33, 2-35, 2-37, 2-38, 2-40, 2-41, 2-42, 2-43, 2-45, 2-47, 2-48, 2-49,2-50, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61,2-62, 2-63, 2-64, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73, 2-74, 2-81,2-82, 2-83, 2-84, 2-85, 2-86, 2-88, 2-89, 2-91, 2-93, 2-94, 2-95, 2-97,2-99, 2-100, 2-101, 2-102, 2-104, 2-107, 2-108, 2-109, 2-112, 2-114,2-115, 2-116, 2-118, 2-119, 2-120, 2-121, 2-124, 2-126, 2-127, 2-128,2-129, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139,2-140, 2-141, 2-142, 2-143, 2-145, 2-146, 2-147, 2-148, 2-149, 2-150,2-151, 2-152, 2-153, 2-154, 2-155, 2-162, 2-163, 2-164, 2-165, 2-166,2-170, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-193,2-195, 2-197, 2-199, 2-200, 2-201, 2-203, 2-204, 2-206, 2-207, 2-208,2-209, 2-210, 2-211, 2-212, 2-213, 2-214, 2-215, 2-216, 2-217, 2-218,2-219, 2-220, 2-222, 2-224, 2-225, 2-226, 2-227, 3-3, 3-4, 3-6, 3-7,3-8, 3-10, 3-11, 3-12, 3-17, 3-18, 3-19, 3-21, 3-23, 3-24, 3-25, 3-26,4-1, 5-2, and 5-3 at 500 ppm, respectively, showed a mortality of atleast 75% in comparison with untreated controls.

B.8 Silverleaf Whitefly (Bemisia argentifolii)

The active compounds were formulated in cyclohexanone as a 10,000 ppmsolution supplied in tubes. The tubes were inserted into an automatedelectrostatic sprayer equipped with an atomizing nozzle and they servedas stock solutions for which lower dilutions were made in 50%acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was includedin the solution at a volume of 0.01% (v/v).

Cotton plants at the cotyledon stage (one plant per pot) were sprayed byan automated electrostatic plant sprayer equipped with an atomizingspray nozzle. The plants were dried in the sprayer fume hood and thenremoved from the sprayer. Each pot was placed into a plastic cup andabout 10 to 12 whitefly adults (approximately 3-5 days old) wereintroduced. The insects were collected using an aspirator and a nontoxicTygon® tubing connected to a barrier pipette tip. The tip, containingthe collected insects, was then gently inserted into the soil containingthe treated plant, allowing insects to crawl out of the tip to reach thefoliage for feeding. Cups were covered with a reusable screened lid.Test plants were maintained in a growth room at about 25° C. and about20-40% relative humidity for 3 days, avoiding direct exposure tofluorescent light (24 hour photoperiod) to prevent trapping of heatinside the cup. Mortality was assessed 3 days after treatment, comparedto untreated control plants.

In this test, the compounds 1-7, 1-9, 1-10, 2-2, 2-3, 2-4, 2-5, 2-10,2-11, 2-12, 2-13, 2-15, 2-23, 2-26, 2-28, 2-29, 2-31, 2-33, 2-35, 2-37,2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-47, 2-48, 2-49, 2-50, 2-53, 2-57,2-58, 2-59, 2-62, 2-63, 2-65, 2-66, 2-67, 2-68, 2-71, 2-72, 2-73, 2-74,2-75, 2-77, 2-81, 2-82, 2-83, 2-84, 2-86, 2-87, 2-88, 2-90, 2-91, 2-92,2-93, 2-95, 2-96, 2-99, 2-100, 2-109, 2-110, 2-114, 2-115, 2-121, 2-123,2-128, 2-130, 2-134, 2-136, 2-137, 2-138, 2-139, 2-140, 2-142, 2-143,2-145, 2-146, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155,2-162, 2-163, 2-164, 2-165, 2-166, 2-169, 2-171, 2-172, 2-173, 2-178,2-179, 2-181, 2-182, 2-183, 2-185, 2-186, 2-188, 2-189, 2-190, 2-195,2-199, 3-1, 3-4, 3-6, 3-7, 3-9, 3-10, 3-11, 3-12, and 3-19 at 100 ppm,respectively, showed a mortality of at least 75% in comparison withuntreated controls.

B.9 Southern Armyworm (Spodoptera eridania)

The active compounds were formulated in cyclohexanone as a 10,000 ppmsolution supplied in tubes. The tubes were inserted into an automatedelectrostatic sprayer equipped with an atomizing nozzle and they servedas stock solutions for which lower dilutions were made in 50%acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was includedin the solution at a volume of 0.01% (v/v).

Lima bean plants (variety Sieva) were grown 2 plants to a pot andselected for treatment at the 1^(st) true leaf stage. Test solutionswere sprayed onto the foliage by an automated electrostatic plantsprayer equipped with an atomizing spray nozzle. The plants were driedin the sprayer fume hood and then removed from the sprayer. Each pot wasplaced into perforated plastic bags with a zip closure. About 10 to 11armyworm larvae were placed into the bag and the bags zipped closed.Test plants were maintained in a growth room at about 25° C. and about20-40% relative humidity for 4 days, avoiding direct exposure tofluorescent light (24 hour photoperiod) to prevent trapping of heatinside the bags. Mortality and reduced feeding were assessed 4 daysafter treatment, compared to untreated control plants.

In this test, the compounds 1-1, 1-2, 1-5, 1-7, 1-8, 1-9, 1-10, 1-11,1-13, 1-14, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11,2-12, 2-13, 2-15, 2-18, 2-19, 2-20, 2-21, 2-23, 2-26, 2-27, 2-28, 2-29,2-30, 2-31, 2-32, 2-33, 2-35, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43,2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-50, 2-51, 2-52, 2-53, 2-54, 2-55,2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67,2-68, 2-69, 2-70, 2-71, 2-72, 2-73, 2-74, 2-75, 2-76, 2-77, 2-81, 2-82,2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91, 2-92, 2-93, 2-94,2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105,2-106, 2-107, 2-108, 2-109, 2-110, 2-112, 2-114, 2-115, 2-116, 2-117,2-118, 2-119, 2-120, 2-121, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128,2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138,2-139, 2-140, 2-141, 2-142, 2-143, 2-144, 2-145, 2-146, 2-147, 2-148,2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-162, 2-163, 2-164,2-165, 2-166, 2-169, 2-170, 2-171, 2-172, 2-173, 2-178, 2-179, 2-180,2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-187, 2-188, 2-189, 2-190,2-191, 2-192, 2-193, 2-195, 2-197, 2-198, 2-199, 2-200, 2-202, 2-203,2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-212, 2-214, 2-216, 2-221,2-222, 2-224, 2-225, 2-226, 2-227, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7,3-8, 3-9, 3-10, 3-11, 3-12, 3-13, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22,3-23, 3-24, 3-25, 3-26, 3-27, 4-1, 5-2, 5-3, 5-6 and 5-7 at 1 ppm,respectively, showed a mortality of at least 75% in comparison withuntreated controls.

B.10 Vetch Aphid (Megoura viciae)

For evaluating control of vetch aphid (Megoura viciae) through contactor systemic means the test unit consisted of 24-well-microtiter platescontaining broad bean leaf disks.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds weresprayed onto the leaf disks at 2.5 μl, using a custom built microatomizer, at two replications.

After application, the leaf disks were air-dried and 5-8 adult aphidsplaced on the leaf disks inside the microtiter plate wells. The aphidswere then allowed to suck on the treated leaf disks and incubated atabout 23±1° C. and about 50±5% relative humidity for 5 days. Aphidmortality and fecundity was then visually assessed.

In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-7, 1-8, 1-9,1-10, 1-12, 1-13, 1-15, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9,2-10, 2-11, 2-12, 2-13, 2-15, 2-19, 2-20, 2-21, 2-23, 2-24, 2-26, 2-27,2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-35, 2-36, 2-37, 2-38, 2-39, 2-40,2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-51, 2-52, 2-53,2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65,2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73, 2-74, 2-75, 2-77, 2-79,2-81, 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91, 2-92,2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101, 2-102, 2-104,2-105, 2-106, 2-107, 2-108, 2-109, 2-110, 2-111, 2-112, 2-114, 2-115,2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-123, 2-124, 2-125, 2-126,2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136,2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143, 2-145, 2-146, 2-147,2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-159, 2-162,2-163, 2-164, 2-165, 2-166, 2-170, 2-171, 2-172, 2-173, 2-178, 2-179,2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-188, 2-189, 2-190,2-191, 2-192, 2-193, 2-194, 2-195, 2-197, 2-198, 2-199, 2-200, 2-201,2-202, 2-203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-211, 2-213,2-214, 2-215, 2-216, 2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223,2-224, 2-225, 2-226, 2-227, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-13,3-14, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-25, 3-26,3-27, 3-28, 4-1, 5-1, 5-2, 5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 2500 ppm,respectively, showed a mortality of at least 75% in comparison withuntreated controls.

B.11 Tobacco Budworm (Heliothis virescens) I

For evaluating control of tobacco budworm (Heliothis virescens) the testunit consisted of 96-well-microtiter plates containing an insect dietand 15-25 H. virescens eggs. The compounds were formulated using asolution containing 75% v/v water and 25% v/v DMSO. Differentconcentrations of formulated compounds were sprayed onto the insect dietat 10 μl, using a custom built micro atomizer, at two replications.

After application, microtiter plates were incubated at about 28±1° C.and about 80±5% relative humidity for 5 days. Egg and larval mortalitywas then visually assessed.

In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-7, 1-8, 1-9,1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7,2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-15, 2-17, 2-18, 2-19, 2-20, 2-21,2-22, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-34, 2-35,2-36, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47,2-48, 2-49, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60,2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72,2-73, 2-74, 2-75, 2-77, 2-78, 2-81, 2-82, 2-83, 2-84, 2-85, 2-86, 2-87,2-88, 2-89, 2-90, 2-91, 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99,2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109,2-110, 2-111, 2-112, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120,2-121, 2-122, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130,2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140,2-141, 2-142, 2-143, 2-147, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153,2-154, 2-155, 2-156, 2-157, 2-158, 2-160, 2-161, 2-162, 2-163, 2-164,2-165, 2-166, 2-167, 2-169, 2-170, 2-171, 2-172, 2-173, 2-174, 2-175,2-177, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186,2-187, 2-188, 2-189, 2-190, 2-191, 2-192, 2-193, 2-194, 2-195, 2-196,2-197, 2-198, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-206, 2-207,2-208, 2-209, 2-210, 2-211, 2-212, 2-213, 2-215, 2-216, 2-217, 2-218,2-219, 2-220, 2-221, 2-222, 2-223, 2-224, 2-225, 2-226, 2-227, 3-3, 3-4,3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-13, 3-14, 3-15, 3-16, 3-17,3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-25, 3-26, 3-27, 3-28, 4-1,5-1, 5-2, 5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 2500 ppm, respectively,showed a mortality of at least 75% in comparison with untreatedcontrols.

B.12 Boll Weevil (Anthonomus grandis)

For evaluating control of boll weevil (Anthonomusgrandis) the test unitconsisted of 24-well-microtiter plates containing an insect diet and20-30 A. grandis eggs.

The compounds were formulated using a solution containing 75% v/v waterand 25% v/v DMSO. Different concentrations of formulated compounds weresprayed onto the insect diet at 20 μl, using a custom built microatomizer, at two replications.

After application, microtiter plates were incubated at about 23±1° C.and about 50±5% relative humidity for 5 days. Egg and larval mortalitywas then visually assessed.

In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-7, 1-8, 1-9,1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7,2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-15, 2-18, 2-19, 2-20, 2-21, 2-22,2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-34, 2-35, 2-36,2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48,2-49, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61,2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73,2-74, 2-75, 2-76, 2-77, 2-78, 2-79, 2-80, 2-81, 2-82, 2-83, 2-84, 2-85,2-86, 2-87, 2-88, 2-89, 2-90, 2-91, 2-92, 2-93, 2-94, 2-95, 2-96, 2-97,2-98, 2-99, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-106, 2-107,2-108, 2-109, 2-110, 2-111, 2-112, 2-113, 2-114, 2-115, 2-116, 2-117,2-118, 2-119, 2-120, 2-121, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128,2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138,2-139, 2-140, 2-141, 2-142, 2-143, 2-145, 2-146, 2-147, 2-148, 2-149,2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-157, 2-158, 2-160, 2-162,2-163, 2-164, 2-165, 2-166, 2-167, 2-168, 2-169, 2-170, 2-171, 2-172,2-173, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186,2-187, 2-188, 2-189, 2-190, 2-191, 2-192, 2-193, 2-194, 2-195, 2-196,2-197, 2-198, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-206, 2-207,2-208, 2-209, 2-210, 2-211, 2-212, 2-213, 2-214, 2-215, 2-216, 2-217,2-218, 2-219, 2-220, 2-221, 2-222, 2-223, 2-224, 2-225, 2-226, 2-227,3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-13, 3-14, 3-15,3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-25, 3-26, 3-27,3-28, 4-1, 5-1, 5-2, 5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 2500 ppm,respectively, showed a mortality of at least 75% in comparison withuntreated controls.

B.13 Colorado Potato Beetle (Leptinotarsa decemlineata)

The active compounds were formulated in cyclohexanone as a 10,000 ppmsolution supplied in tubes. The tubes were inserted into an automatedelectrostatic sprayer equipped with an atomizing nozzle and they servedas stock solutions for which lower dilutions were made in 50%acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was includedin the solution at a volume of 0.01% (v/v).

Eggplants were grown 2 plants to a pot and were selected for treatmentat the 1^(st) true leaf stage. Test solutions were sprayed onto thefoliage by an automated electrostatic plant sprayer equipped with anatomizing spray nozzle. The plants were dried in the sprayer fume hoodand then removed from the sprayer. The treated foliage was then cut andremoved from the pot and placed in a 5-inch Petri dish lined withmoistened filter paper. Five beetle larvae were introduced into eachPetri dish and the dish was covered by a Petri dish lid. Petri disheswere maintained in a growth room at 25° C. and 20-40% relative humidityfor 4 days, avoiding direct exposure to fluorescent light (24 hourphotoperiod) to prevent trapping of heat inside the dishes. Mortalityand reduced feeding were assessed 4 days after treatment, compared tountreated control plants.

In this test, the compounds 1-2, 2-1, 2-4, 2-5, 2-6, 2-10, 2-11, 2-12,2-13, 2-19, 2-20, 2-26, 2-27, 2-28, 2-31, 2-32, 2-33, 2-35, 2-37, 2-38,2-40, 2-43, 2-49, 2-50, 2-53, 2-57, 2-58, 2-59, 2-61, 2-67, 2-68, 2-71,2-72, 2-73, 2-74, 2-82, 2-83, 2-88, 2-89, 2-93, 2-108, 2-112, 2-116,2-118, 2-119, 2-120, 2-124, 2-126, 2-127, 2-128, 2-129, 2-131, 2-132,2-133, 2-135, 2-137, 2-138, 2-141, 2-143, 2-147, 2-148, 2-149, 2-150,2-151, 2-153, 2-154, 2-155, 2-162, 2-163, 2-165, 2-170, 2-178, 2-179,2-180, 2-181, 2-182, 2-185, 2-186, 2-187, 2-193, 2-197, 2-199, 2-200,3-4, 3-5, 3-7, 3-8, 3-9, 3-17, and 3-18 at 1 ppm, respectively, showed amortality of at least 75% in comparison with untreated controls.

B.14 Red Spider Mite (Tetranychus kanzawai)

The active compound was dissolved at the desired concentration in amixture of 1:1 (v/v) distilled water:acetone. A surfactant (Alkamuls® EL620) was added at the rate of 0.1% (v/v).

Potted cowpea beans of 7-10 days of age were cleaned with tap water andsprayed with 5 ml of the test solution using air driven hand atomizer.The treated plants were allowed to air dry and afterwards inculated with20 or more mites by clipping a cassava leaf section with known mitepopulation. Treated plants were placed inside a holding room at about25-27° C. and about 50-60% relatice humidity.

Mortality was determined by counting the live mites 72 HAT. Percentmortality was assessed after 72 h.

In this test, the compounds 2-1, 2-2, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9,2-10, 2-12, 2-13, 2-15, 2-26, 2-27, 2-28, 2-29, 2-30, 2-32, 2-37, 2-40,2-43, 2-48, 2-51, 2-54, 2-55, 2-59, 2-60, 2-68, 2-70, 2-71, 2-72, 2-73,2-75, 2-77, 2-82, 2-86, 2-97, 2-98, 2-99, 2-100, 2-108, 2-116, 2-118,2-119, 2-120, 2-124, 2-126, 2-127, 2-128, 2-129, 2-131, 2-132, 2-133,2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143,2-145, 2-146, 2-147, 2-148, 2-149, 2-151, 2-153, 2-162, 2-165, 2-166,2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-193,2-195, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-206, 2-207, 2-208,2-209, 2-210, 2-211, 2-213, 2-214, 2-215, 2-216, 2-217, 2-218, 2-219,2-220, 2-221, 2-222, 2-224, 2-225, 2-226, 3-1, 3-7, 3-8, 3-10, 3-11,3-12, 3-21, 3-22, 3-23, 3-24, 5-1, 5-2, and 5-3 at 500 ppm,respectively, showed a mortality of at least 75% in comparison withuntreated controls.

We claim:
 1. A compound of formula I

wherein A is a group A¹ or A³; wherein A¹ is selected from the groupconsisting of —C(═NR⁶)R⁸, and —S(O)_(n)R⁹; A³ is a group of followingformula:

wherein # denotes the bond to the aromatic ring of formula (I); B¹, B²and B³ are each independently selected from the group consisting of Nand CR², with the proviso that at most two of B¹, B² and B³ are N; G¹,G², G³ and G⁴ are each independently selected from the group consistingof N and CR⁴, with the proviso that at most two of G¹, G², G³ and G⁴ areN; R¹ is CF₃; each R² is independently selected from the groupconsisting of hydrogen, halogen, cyano, azido, nitro, —SCN, —SF₅,C₁-C₆-alkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein thefour last mentioned aliphatic and cycloaliphatic radicals may bepartially or fully halogenated and/or may be substituted by one or moreradicals R⁸, —Si(R¹²)₃, —OR⁹, —S(O)_(n)R⁹, —NR^(10a)R^(10b), phenylwhich may be substituted by 1, 2, 3, 4 or 5 radicals R¹¹, and a 3-, 4-,5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated ormaximally unsaturated heteromonocyclic or heterobicyclic ring containing1, 2, 3 or 4 heteroatoms or heteroatom groups selected from the groupconsisting of N, O, S, NO, SO and SO₂, as ring members, where theheteromono- or heterobicyclic ring may be substituted by one or moreradicals R¹¹; R^(3a), R^(3b) are each independently selected from thegroup consisting of hydrogen, halogen, hydroxyl, —CO₂R^(3d),C₁-C₃-alkyl, C₁-C₃-haloalkyl, C₂-C₃-alkenyl, C₂-C₃-alkynyl,C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio,C₁-C₃-alkylsulfonyl and C₁-C₃-haloalkylsulfonyl; or R^(3a) and R^(3b)together form a group ═O, ═C(R^(3c))₂, ═NOH or ═NOCH₃; each R^(3c) isindependently selected from the group consisting of hydrogen, halogen,CH₃ and CF₃; R^(3d) is selected from the group consisting of hydrogen,C₁-C₆-alkyl and C₁-C₃-alkyloxy-C₁-C₃-alkyl-; each R⁴ is independentlyselected from the group consisting of hydrogen, halogen, cyano, azido,nitro, —SCN, —SF₅, C₁-C₆-alkyl which may be partially or fullyhalogenated and/or may be substituted by one or more radicals R⁸,C₃-C₈-cycloalkyl which may be partially or fully halogenated and/or maybe substituted by one or more radicals R⁸, C₂-C₆-alkenyl which may bepartially or fully halogenated and/or may be substituted by one or moreradicals R⁸, C₂-C₆-alkynyl which may be partially or fully halogenatedand/or may be substituted by one or more radicals R⁸, —Si(R¹²)₃, —OR⁹,—S(O)R⁹, —NR^(10a)R^(10b), phenyl which may be substituted by 1, 2, 3, 4or 5 radicals R¹¹, and a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-memberedsaturated, partially unsaturated or maximally unsaturatedheteromonocyclic or heterobicyclic ring containing 1, 2, 3 or 4heteroatoms or heteroatom groups selected from the group consisting ofN, O, S, NO, SO and SO₂, as ring members, where the heteromonocyclic orheterobicyclic ring may be substituted by one or more radicals R¹¹; eachR⁵ is independently selected from the group consisting of hydrogen,C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, whereinthe four last-mentioned aliphatic and cycloaliphatic radicals may bepartially or fully halogenated and/or may be substituted with one ormore substituents R⁸, and —S(O)_(n)R⁹, each R⁶ is independently selectedfrom the group consisting of hydrogen, cyano, C₁-C₁₀-alkyl,C₃-C₈-cycloalkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the fourlast-mentioned aliphatic and cycloaliphatic radicals may be partially orfully halogenated and/or may be substituted by one or more substituentsR⁸, —OR⁹, —NR^(10a)R^(10b), —S(O)_(n)R⁹,—C(═O)NR^(10a)N(R^(10a)R^(10b)), —Si(R¹²)₃, —C(═O)R⁸, phenyl which maybe substituted with 1, 2, 3, 4, or 5 substituents R¹¹, and a 3-, 4-, 5-,6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated ormaximally unsaturated heteromonocyclic or heterobicyclic ring containing1, 2, 3 or 4 heteroatoms or heteroatom groups independently selectedfrom the group consisting of N, O, S, NO, SO and SO₂, as ring members,where the heteromonocyclic or heterobicyclic ring may be substitutedwith one or more substituents R¹¹; or R⁵ and R⁶, together with thenitrogen atom to which they are bound, form a 3-, 4-, 5-, 6-, 7- or8-membered saturated, partially unsaturated or maximally unsaturatedheterocyclic ring, where the ring may further contain 1, 2, 3 or 4heteroatoms or heteroatom-containing groups selected from the groupconsisting of O, S, N, SO, SO₂, C═O and C═S as ring members, wherein theheterocyclic ring may be substituted with 1, 2, 3, 4 or 5 substituentsindependently selected from the group consisting of halogen, cyano,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, wherein the aliphatic or cycloaliphatic moieties inthe twelve last-mentioned radicals may be substituted by one or moreradicals R⁸, and phenyl which may be substituted with 1, 2, 3, 4 or 5substituents R¹¹; or R⁵ and R⁶ together form a group ═C(R⁸)₂,═S(O)_(m)(R⁹)₂, ═NR^(10a) or ═NOR⁹; R^(7a), R^(7b) are eachindependently selected from the group consisting of hydrogen, halogen,cyano, C₁-C₆-alkyl, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl,wherein the four last-mentioned aliphatic and cycloaliphatic radicalsmay be partially or fully halogenated and/or may be substituted by oneor more radicals R⁸; each R⁸ is independently selected from the groupconsisting of cyano, azido, nitro, —SCN, —SF₅, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, where the cycloaliphatic moieties in the twolast-mentioned radicals may be substituted by one or more radicals R¹³;—Si(R¹²)₃, —OR⁹, —OSO₂R⁹, —S(O)_(n)R⁹, —N(R^(10a))R^(10b),—C(═O)N(R^(10a))R^(10b), —C(═S)N(R^(10a))R^(10b), —C(═O)OR⁹, phenyl,optionally substituted with 1, 2, 3, 4 or 5 substituents R¹⁶, and a 3-,4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximallyunsaturated heterocyclic ring comprising 1, 2 or 3 heteroatoms orheteroatom groups selected from the group consisting of N, O, S, NO, SOand SO₂, as ring members, where the heterocyclic ring is optionallysubstituted with one or more substituents R¹⁶, or two R⁸ present on thesame carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyl grouptogether form a group ═O, ═C(R¹³)₂; ═S; ═S(O)_(m)(R¹⁵)₂,═S(O)_(m)R¹⁵N(R^(14a))R^(14b), ═NR^(10a), ═NOR⁹; or ═NN(R^(10a))R^(10b);or two radicals R⁸, together with the carbon atoms of an alkyl, alkenyl,alkynyl or cycloalkyl group which they are bonded to, form a 3-, 4-, 5-,6-, 7- or 8-membered saturated or partially unsaturated carbocyclic orheterocyclic ring, where the heterocyclic ring comprises 1, 2, 3 or 4heteroatoms or heteroatom groups independently selected from N, O, S,NO, SO and SO₂, as ring members, and where the carbocyclic orheterocyclic ring is optionally substituted with one or moresubstituents R¹⁶; and R⁸ as a substituent on a cycloalkyl ring isadditionally selected from the group consisting of C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl andC₂-C₆-haloalkynyl, where the aliphatic moieties in these six radicalsmay be substituted by one or more radicals R¹³; and R⁸ in the groups—C(═NR⁶)R⁸, —C(═O)R⁸ and ═C(R⁸)₂ is additionally selected from the groupconsisting of hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl and C₂-C₆-haloalkynyl,where the aliphatic moieties in the six last-mentioned radicals may besubstituted by one or more radicals R¹³; each R⁹ is independentlyselected from the group consisting of hydrogen, cyano, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl-,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, where the aliphatic and cycloaliphatic moieties inthe nine last-mentioned radicals may be substituted by one or moreradicals R¹³, —C₁-C₆-alkyl-C(═O)OR¹⁵,—C₁-C₆-alkyl-C(═O)N(R^(14a))R^(14b),—C₁-C₆-alkyl-C(═S)N(R^(14a))R^(14b),—C₁-C₆-alkyl-C(═NR¹⁴)N(R^(14a))R^(14b), —Si(R¹²)₃, —S(O)_(n)R¹⁵,—S(O)_(n)N(R^(14a))R^(14b), —N(R^(10a))R^(10b), —N═C(R¹³)₂, —C(═O)R¹³,—C(═O)N(R^(14a))R^(14b), —C(═S)N(R^(14a))R^(14b), —C(═O)OR¹⁵, phenyl,optionally substituted with one or more substituents R¹⁶; and a 3-, 4-,5-, 6- or 7-membered saturated, partially unsaturated or maximallyunsaturated heterocyclic ring comprising 1, 2 or 3 heteroatoms orheteroatom groups selected from the group consisting of N, O, S, NO, SOand SO₂, as ring members, where the heterocyclic ring is optionallysubstituted with one or more substituents R¹⁶; and R⁹ in the groups—S(O)_(n)R⁹ and —OSO₂R⁹ is additionally selected from the groupconsisting of C₁-C₆-alkoxy and C₁-C₆-haloalkoxy; R^(10a), R^(10b) areselected independently from one another from the group consisting ofhydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, where the aliphatic and cycloaliphatic moieties inthe eight last-mentioned radicals may be substituted by one or moreradicals R¹³; —C₁-C₆-alkyl-C(═O)OR¹⁵,—C₁-C₆-alkyl-C(═O)N(R^(14a))R^(14b),—C₁-C₆-alkyl-C(═S)N(R^(14a))R^(14b),—C₁-C₆-alkyl-C(═NR¹⁴)N(R^(14a))R^(14b), C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, —S(O)_(n)R¹⁵,—S(O)_(n)N(R^(14a))R^(14b), —C(═O)R¹³, —C(═O)OR¹⁵,—C(═O)N(R^(14a))R^(14b), —C(═S)R¹³, —C(═S)SR¹⁵, —C(═S)N(R^(14a))R^(14b),—C(═NR¹⁴)R¹³; phenyl, optionally substituted with 1, 2, 3 or 4,substituents R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated,partially unsaturated or maximally unsaturated heterocyclic ringcomprising 1, 2, 3 or 4 heteroatoms or heteroatom groups selected fromN, O, S, NO, SO and SO₂, as ring members, where the heterocyclic ring isoptionally substituted with one or more substituents R¹⁶; or R^(10a) andR^(10b) form together with the nitrogen atom they are bonded to a 3-,4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated ormaximally unsaturated heterocyclic ring, wherein the heterocyclic ringmay additionally contain one or two heteroatoms or heteroatom groupsselected from N, O, S, NO, SO and SO₂, as ring members, where theheterocyclic ring optionally carries one or more substituents selectedfrom halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl, optionallysubstituted with 1, 2, 3, 4 or 5 substituents R¹⁶, and a 3-, 4-, 5-, 6,-or 7-membered saturated, partially unsaturated or maximally unsaturatedheterocyclic ring comprising 1, 2 or 3 heteroatoms or heteroatom groupsselected from the group consisting of N, O, S, NO, SO and SO₂, as ringmembers, where the heterocyclic ring optionally carries one or moresubstituents R¹⁶; or R^(10a) and R^(10b) together form a group ═C(R¹³)₂,═S(O)_(m)(R¹⁵)₂, ═S(O)_(m)R¹⁵N(R^(14a))R^(14b), ═NR¹⁴ or ═NOR¹⁵; R¹¹ isindependently selected from the group consisting of halogen, cyano,azido, nitro, —SCN, —SF₅, C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the four last-mentionedaliphatic and cycloaliphatic radicals may be partially or fullyhalogenated and/or may be substituted with one or more radicals R⁸,—OR⁹, —NR^(10a)R^(10b), —S(O)_(n)R⁹, —Si(R¹²)₃; phenyl, optionallysubstituted with 1, 2, 3, 4, or 5 substituents selected independentlyfrom R¹⁶; and a 3-, 4-, 5-, 6- or 7-membered saturated, partiallyunsaturated or maximally unsaturated aromatic heterocyclic ringcomprising 1, 2, 3 or 4 heteroatoms or heteroatom groups selected fromthe group consisting of N, O, S, NO, SO and SO₂, as ring members, wherethe heterocyclic ring is optionally substituted with one or moresubstituents selected independently from R¹⁶; or two R¹¹ present on thesame ring carbon atom of a saturated or partially unsaturatedheterocyclic ring may together form a group ═O, ═C(R¹³)₂; ═S;═S(O)_(m)(R¹⁵)₂; ═S(O)_(m)R¹⁵N(R^(14a))R^(14b), —NR¹⁴, —NOR¹⁵, or═NN(R^(14a))R^(14b); or two R¹¹ bound on adjacent ring atoms formtogether with the ring atoms to which they are bound a saturated 3-, 4-,5-, 6-, 7-, 8- or 9-membered ring, wherein the ring may contain 1 or 2heteroatoms or heteroatom groups selected from O, S, N, NR¹⁴, NO, SO andSO₂ and/or 1 or 2 groups selected from C═O, C═S and C═NR¹⁴ as ringmembers, and wherein the ring may be substituted by one or more radicalsselected from the group consisting of halogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R¹⁶, and a3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated ormaximally unsaturated heterocyclic ring containing 1, 2 or 3 heteroatomsor heteroatom groups selected from the group consisting of N, O, S, NO,SO and SO₂, as ring members, where the heterocyclic ring may besubstituted by one or more radicals R¹⁶; each R¹² is independentlyselected from the group consisting of hydrogen, halogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-haloalkoxy-C₁-C₆-alkyl, and phenyl, optionally substituted with 1,2, 3, 4, or 5 substituents R¹⁶; each R¹³ is independently selected fromthe group consisting of cyano, nitro, —OH, —SH, —SCN, —SF₅,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, trimethylsilyl, triethylsilyl,tert-butyldimethylsilyl, C₃-C₈-cycloalkyl which may be unsubstituted,partially or fully halogenated and/or may carry 1 or 2 radicals selectedfrom C₁-C₄-alkyl, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy andoxo; phenyl, benzyl, phenoxy, where the phenyl moiety in the threelast-mentioned radicals may be unsubstituted or carry 1, 2, 3, 4 or 5substituents R¹⁶; and a 3-, 4-, 5-, 6-, or 7-membered saturated,partially unsaturated or maximally unsaturated heterocyclic ringcontaining 1, 2 or 3 heteroatoms or heteroatom groups selected from thegroup consisting of N, O, S, NO, SO and SO₂, as ring members, where theheterocyclic ring may be substituted by 1, 2 or 3 substituents R¹⁶; ortwo R¹³ present on the same carbon atom of an alkyl, alkenyl, alkynyl orcycloalkyl group may together be ═O, ═CH(C₁-C₄-alkyl),═C(C₁-C₄-alkyl)C₁-C₄-alkyl, ═N(C₁-C₆-alkyl) or ═NO(C₁-C₆-alkyl); and R¹³as a substituent on a cycloalkyl ring is additionally selected from thegroup consisting of C₁-C₆-alkyl, C₂-C₆-alkenyl and C₂-C₆-alkynyl,wherein the three last-mentioned aliphatic radicals may beunsubstituted, partially or fully halogenated and/or may carry 1 or 2substituents selected from CN, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy and oxo; and R¹³ in the groups ═C(R¹³)₂, —N═C(R¹³)₂,—C(═O)R¹³, —C(═S)R¹³ and —C(═NR¹⁴)R¹³ is additionally selected from thegroup consisting of hydrogen, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl andC₂-C₆-alkynyl, wherein the three last-mentioned aliphatic radicals maybe unsubstituted, partially or fully halogenated and/or may carry 1 or 2radicals selected from CN, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy and oxo; each R¹⁴ is independently selected from thegroup consisting of hydrogen, cyano, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl,trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the three last-mentioned aliphaticradicals may be unsubstituted, partially or fully halogenated and/or maycarry 1 or 2 radicals selected from oxo, CN, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,C₁-C₄-alkylsulfonyl, C₃-C₄-cycloalkyl which may be substituted by 1 or 2substituents selected from halogen and cyano; C₃-C₈-cycloalkyl which maybe unsubstituted, partially or fully halogenated and/or may carry 1 or 2radicals selected from oxo C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl,C₃-C₄-cycloalkyl, C₃-C₄-cycloalkyl-C₁-C₄-alkyl-, where the cycloalkylmoiety in the two last-mentioned radicals may be substituted by 1 or 2substituents selected from halogen and cyano; phenyl, benzyl, pyridyl,phenoxy, wherein the cyclic moieties in the four last-mentioned radicalsmay be unsubstituted or carry 1, 2 or 3 substituents selected fromhalogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxyand (C₁-C₆-alkoxy)carbonyl; and a 3-, 4-, 5- or 6-membered saturated,partially unsaturated or maximally unsaturated heterocyclic ringcomprising 1 or 2 heteroatoms or heteroatom groups selected from thegroup consisting of N, O, S, NO, SO and SO₂, as ring members, where theheterocyclic ring is optionally substituted with one or moresubstituents R¹⁶; R^(14a) and R^(14b), independently of each other, haveone of the meanings given for R¹⁴; or R^(14a) and R^(14b), together withthe nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or7-membered saturated, partially unsaturated or maximally unsaturatedheterocyclic ring, wherein the heterocyclic ring may additionallycontain 1 or 2 heteroatoms or heteroatom groups selected from the groupconsisting of N, O, S, NO, SO and SO₂, as ring members, where theheterocyclic ring optionally carries one or more substituents selectedfrom halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy; or R^(14a) and R¹⁴ or R^(14b) and R¹⁴, together withthe nitrogen atoms to which they are bound in the group—C(═NR¹⁴)N(R^(14a))R^(14b), form a 3-, 4-, 5-, 6- or 7-memberedpartially unsaturated or maximally unsaturated heterocyclic ring,wherein the heterocyclic ring may additionally contain 1 or 2heteroatoms or heteroatom groups selected from the group consisting ofN, O, S, NO, SO and SO₂, as ring members, where the heterocyclic ringoptionally carries one or more substituents selected from halogen,C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; each R¹⁵ isindependently selected from the group consisting of hydrogen, cyano,trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the three last-mentioned aliphaticradicals may be unsubstituted, partially or fully halogenated and/or maycarry 1 or 2 radicals selected from C₃-C₄-cycloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,C₁-C₄-alkylsulfonyl and oxo; C₃-C₈-cycloalkyl which may beunsubstituted, partially or fully halogenated and/or may carry 1 or 2radicals selected from C₁-C₄-alkyl, C₃-C₄-cycloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,C₁-C₄-alkylsulfonyl and oxo; phenyl, benzyl, pyridyl and phenoxy,wherein the four last-mentioned radicals may be unsubstituted, partiallyor fully halogenated and/or carry 1, 2 or 3 substituents selected fromC₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and(C₁-C₆-alkoxy)carbonyl; each R¹⁶ is independently selected from thegroup consisting of halogen, nitro, cyano, —OH, —SH, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, trimethylsilyl, triethylsilyl,tert-butyldimethylsilyl; C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,wherein the three last-mentioned aliphatic radicals may beunsubstituted, partially or fully halogenated and/or may carry 1 or 2radicals selected from C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxyand oxo; C₃-C₈-cycloalkyl which may be unsubstituted, partially or fullyhalogenated and/or may carry 1 or 2 radicals selected from C₁-C₄-alkyl,C₃-C₄-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy and oxo; phenyl,benzyl, pyridyl and phenoxy, wherein the four last mentioned radicalsmay be unsubstituted, partially or fully halogenated and/or carry 1, 2or 3 substituents selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and (C₁-C₆-alkoxy)carbonyl; or two R¹⁶present together on the same atom of a saturated or partiallyunsaturated ring may be ═O, ═S, ═N(C₁-C₆-alkyl), ═NO(C₁-C₆-alkyl),═CH(C₁-C₄-alkyl) or ═C(C₁-C₄-alkyl)C₁-C₄-alkyl; or two R¹⁶ on twoadjacent carbon atoms form together with the carbon atoms they arebonded to a 4-, 5-, 6-, 7- or 8-membered saturated, partiallyunsaturated or maximally unsaturated ring, wherein the ring may contain1 or 2 heteroatoms or heteroatom groups selected from the groupconsisting of N, O, S, NO, SO and SO₂, as ring members, and wherein thering optionally carries one or more substituents selected from halogen,C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; each n isindependently 0, 1 or 2; and each m is independently 0 or 1; an N-oxide,stereoisomer or agriculturally or veterinarily acceptable salt thereof.2. The compound as claimed in claim 1, where A is A¹ and A¹ is—C(═NR⁶)R⁸.
 3. The compound as claimed in claim 2, where R⁶ in—C(═NR⁶)R⁸ is selected from hydrogen, cyano, C₃-C₈-cycloalkyl,C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, wherein the four last-mentionedaliphatic and cycloaliphatic radicals each independently may bepartially or fully halogenated and/or may be substituted with 1, 2, 3,4, 5 or 6 substituents R⁸; —OR⁹ and —NR^(10a)R^(10b).
 4. The compound asclaimed in claim 3, where R⁶ in —C(═NR⁶)R⁸ is selected from —OR⁹ and—NR^(10a)R^(10b).
 5. The compound as claimed in claim 2, where R⁹ isselected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyland C₂-C₆-haloalkynyl.
 6. The compound as claimed in claim 2, where R⁶in —C(═NR⁶)R⁸ is —NR^(10a)R^(10b), where R^(10a) and R^(10b),independently of each other, are selected from the group consisting ofhydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl,—C(═O)OR¹⁵, —C(═O)N(R^(14a))R^(14b), —C(═S)N(R^(14a))R^(14b), phenylwhich is optionally substituted with 1, 2, 3 or 4, substituents R¹⁶, anda 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated ormaximally unsaturated heterocyclic ring comprising 1, 2, 3 or 4heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO₂,as ring members, where the heterocyclic ring is optionally substitutedwith one or more substituents R¹⁶; or R^(10a) and R^(10b) form togetherwith the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or8-membered saturated, partially unsaturated or maximally unsaturatedheterocyclic ring, wherein the heterocyclic ring may additionallycontain one or two heteroatoms or heteroatom groups selected from thegroup consisting of N, O, S, NO, SO and SO₂, as ring members, where theheterocyclic ring optionally carries one or more substituents selectedfrom halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl and C₂-C₆-haloalkynyl.
 7. The compoundas claimed in claim 6, where R^(10a) is selected from hydrogen,C₁-C₆-alkyl and C₁-C₆-haloalkyl; and R^(10b) is selected fromC₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl,C₁-C₆-haloalkylcarbonyl, —C(═O)OR¹⁵, —C(═O)N(R^(14a))R^(14b),—C(═S)N(R^(14a))R^(14b), phenyl which is optionally substituted with 1,2, 3 or 4, substituents R¹⁶, and a 5- or 6-membered heteroaromatic ringcomprising 1, 2 or 3 heteroatoms selected from N, O and S, as ringmembers, where the heteroaromatic ring is optionally substituted withone or more substituents R¹⁶.
 8. The compound as claimed in claim 6,where R^(14a) is selected from hydrogen, C₁-C₆-alkyl andC₁-C₆-haloalkyl; and R^(14b) is selected from hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,C₂-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl-, C₁-C₆-alkyl substituted with a CN group,C₁-C₆-alkoxyl, C₁-C₆-haloalkoxy, phenyl which is optionally substitutedwith 1, 2, or 3, substituents each independently selected from the groupconsisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, andC₁-C₄-haloalkoxy; and a heterocyclic ring selected from rings offormulae E-1 to E-34 and E-43 to E-51

wherein k is 0, 1, 2 or 3, n is 0, 1 or 2; and each R¹⁶ is independentlyselected from the group consisting of halogen, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyland C₂-C₄-haloalkynyl; or two R¹⁶ present on the same carbon atom of asaturated ring may form together ═O or ═S.
 9. The compound as claimed inclaim 4, where R⁶ in —C(═NR⁶)R⁸ is —NR^(10a)R^(10b), where R^(10a) andR^(10b), independently of each other, are selected from the groupconsisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl,—C(═O)N(R^(14a))R^(14b), —C(═S)N(R^(14a))R^(14b), phenyl which isoptionally substituted with 1, 2, 3 or 4, substituents R¹⁶, and a 3-,4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximallyunsaturated heterocyclic ring comprising 1, 2, 3 or 4 heteroatoms orheteroatom groups selected from the group consisting of N, O, S, NO, SOand SO₂, as ring members, where the heterocyclic ring is optionallysubstituted with one or more substituents R¹⁶; or R^(10a) and R^(10b)form together with the nitrogen atom they are bonded to a 3-, 4-, 5-,6-, 7- or 8-membered saturated, partially unsaturated or maximallyunsaturated heterocyclic ring, wherein the heterocyclic ring mayadditionally contain one or two heteroatoms or heteroatom groupsselected from N, O, S, NO, SO and SO₂, as ring members, where theheterocyclic ring optionally carries one or more substituents selectedfrom halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl and C₂-C₆-haloalkynyl.
 10. The compoundas claimed in claim 9, where R^(10a) is selected from hydrogen,C₁-C₆-alkyl and C₁-C₆-haloalkyl; and R^(10b) is selected from—C(═O)N(R^(14a))R^(14b), —C(═S)N(R^(14a))R^(14b), phenyl which isoptionally substituted with 1, 2, 3 or 4, substituents R¹⁶, and a 5- or6-membered heteroaromatic ring comprising 1, 2 or 3 heteroatoms selectedfrom the group consisting of N, O and S, as ring members, where theheteroaromatic ring is optionally substituted with one or moresubstituents R¹⁶.
 11. The compound as claimed in claim 9, where R^(14a)is selected from the group consisting of hydrogen, C₁-C₆-alkyl andC₁-C₆-haloalkyl; and R^(14b) is selected from the group consisting ofhydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₆-alkylsubstituted with a CN group, phenyl which is optionally substituted with1, 2, or 3, substituents each independently selected from the groupconsisting of halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy and(C₁-C₆-alkoxy)carbonyl; and a heterocyclic ring selected from rings offormulae E-1 to E-34 and E-43 to E-51

wherein k is 0, 1, 2 or 3, n is 0, 1 or 2; and each R¹⁶ is independentlyselected from the group consisting of halogen, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyland C₂-C₄-haloalkynyl; or two R¹⁶ present on the same carbon atom of asaturated ring may form together ═O or ═S.
 12. The compound as claimedin claim 2, where R⁸ in —C(═NR⁶)R⁸ as a meaning for A¹ is selected fromhydrogen and NR^(10a)R^(10b).
 13. The compound as claimed in claim 1,where A is A³ and in A³R^(7a) and R^(7b) are independently of each otherselected from hydrogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl.
 14. Thecompound as claimed in claim 1, where in A³ R⁵ is selected from thegroup consisting of hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the four last-mentioned aliphaticand cycloaliphatic radicals may be partially or fully halogenated and/ormay be substituted with one or more substituents R⁸; and R⁶ is selectedfrom hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, wherein the four last-mentioned aliphatic andcycloaliphatic radicals may be partially or fully halogenated and/or maybe substituted by one or more substituents R⁸, —OR⁹, —NR^(10a)R^(10b),—S(O)_(n)R⁹, —C(═O)NR^(10a)N(R^(10a)R^(10b)), —C(═O)R⁸, and a 3-, 4-,5-, 6- or 7-membered saturated, partially unsaturated or maximallyunsaturated heteromonocyclic or heterobicyclic ring containing 1, 2, 3or 4 heteroatoms or heteroatom groups independently selected from N, O,S, NO, SO and SO₂, as ring members, where the heteromonocyclic orheterobicyclic ring may be substituted with one or more substituentsR¹¹; or R⁵ and R⁶, together with the nitrogen atom to which they arebound, form a 3-, 4-, 5- or 6-membered saturated, partially unsaturatedor maximally unsaturated heterocyclic ring, where the ring may furthercontain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groupsselected from the group consisting of O, S, N, SO, SO₂, C═O and C═S asring members, wherein the heterocyclic ring may be substituted with 1,2, 3, 4 or 5 substituents independently selected from the groupconsisting of halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, wherein thealiphatic or cycloaliphatic moieties in the twelve last-mentionedradicals may be substituted by one or more radicals R⁸, and phenyl whichmay be substituted with 1, 2, 3, 4 or 5 substituents R¹¹; or R⁵ and R⁶together form a group ═C(R⁸)₂, ═S(O)_(m)(R⁹)₂, ═NR^(10a) or ═NOR⁹. 15.The compound as claimed in claim 14, where R⁵ is selected from the groupconsisting of hydrogen, C₁-C₄-alkyl, C₂-C₃-alkynyl, —CH₂—CN andC₁-C₆-alkoxy-methyl; and R⁶ is —C(═O)R⁸.
 16. The compound as claimed inclaim 14, where R⁸ is selected from the group consisting of C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, where thealiphatic and cycloaliphatic moieties in the four last-mentionedradicals may be substituted by one or more radicals R¹³; —OR⁹,—S(O)_(n)R⁹, —N(R^(10a))R^(10b), phenyl, optionally substituted with 1,2, 3, 4 or 5 substituents R¹⁶, and a 3-, 4-, 5- or 6-membered saturated,partially unsaturated or maximally unsaturated heterocyclic ringcomprising 1, 2 or 3 heteroatoms or heteroatom groups selected from thegroup consisting of N, O, S, NO, SO and SO₂, as ring members, where theheterocyclic ring is optionally substituted with one or moresubstituents R¹⁶.
 17. The compound as claimed in claim 16, where R⁸ isselected from the group consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₄-alkyl substituted by one radical R¹³, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, —N(R^(10a))R^(10b), phenyl which is optionallysubstituted with 1, 2, 3, 4 or 5 substituents each independentlyselected from the group consisting of halogen, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyland C₂-C₄-haloalkynyl; and a heterocyclic ring selected from rings offormulae E-1 to E-51,

wherein k is 0, 1, 2 or 3, n is 0, 1 or 2; R^(10a) and R^(10b),independently of each other, are selected from the group consisting ofhydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₃-C₆-cycloalkyl; and R¹³ isselected from CN, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl and a heterocyclic ringselected from rings of formulae E-1 to E-51; and each R¹⁶ as asubstituent on heterocyclic rings of formulae E-1 to E-51 isindependently selected from the group consisting of halogen, cyano,nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₃-C₆-cycloalkyl,C₃-C₆-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyland C₂-C₄-haloalkynyl; or two R¹⁶ present on the same carbon atom of asaturated heterocyclic ring may form together ═O or ═S.
 18. The compoundas claimed in claim 14, where R⁵ and R⁶ are hydrogen.
 19. The compoundas claimed in claim 1, where B¹, B² and B³ are CR².
 20. The compound asclaimed in claim 19, where B¹ and B³ are CR², where R² is not hydrogen,and B² is CR².
 21. The compound as claimed in claim 1, where R² isselected from the group consisting of hydrogen, halogen, cyano, azido,nitro, —SCN, —SF₅, C₃-C₈-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,wherein the four last mentioned aliphatic and cycloaliphatic radicalsmay be partially or fully halogenated and/or may be substituted by oneor more radicals R⁸, —OR⁹, —S(O)_(n)R⁹ and —NR^(10a)R^(10b).
 22. Thecompound as claimed in claim 21, where R² is selected from the groupconsisting of hydrogen, halogen and C₁-C₂-haloalkyl.
 23. The compound asclaimed in claim 1, where G¹, G², G³ and G⁴ are CR⁴; or G¹, G³ and G⁴are CR⁴ and G² is N; or G², G³ and G⁴ are CR⁴ and G¹ is N.
 24. Thecompound as claimed in claim 23, where G¹, G³ and G⁴ are CH and G² isCR⁴.
 25. The compound as claimed in claim 23, where G¹ is N or CH, G³and G⁴ are CH and G² is CR⁴.
 26. The compound as claimed in claim 1,where R⁴ is selected from the group consisting of hydrogen, halogen,cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₅-cycloalkyl,C₃-C₅-halocycloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,C₂-C₄-haloalkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio andC₁-C₄-haloalkylthio.
 27. The compound as claimed in claim 1, whereR^(3a) and R^(3b) are selected, independently of each other, fromhydrogen and halogen.
 28. An agricultural composition comprising atleast one compound of the formula I, as defined in claim 1, astereoisomer thereof or at least one agriculturally acceptable saltthereof, and at least one inert liquid and/or solid agriculturallyacceptable carrier.
 29. A veterinary composition comprising at least onecompound of the formula I, as defined in claim 1, a stereoisomer thereofand/or at least one veterinarily acceptable salt thereof, and at leastone inert liquid and/or solid veterinarily acceptable carrier.
 30. Amethod for controlling invertebrate pests which method comprisestreating the pests, their food supply, their habitat or their breedingground or a plant, plant propagation material, soil, area, material orenvironment in which the pests are growing or may grow, or thematerials, plants, plant propagation material, soils, surfaces or spacesto be protected from invertebrate pest attack or infestation with apesticidally effective amount of at least one imine compound of theformula I as defined in claim 1, a stereoisomer thereof and/or at leastone agriculturally acceptable salt thereof.
 31. The method as claimed inclaim 30, for protecting plants from attack or infestation byinvertebrate pests, which method comprises treating the plants with apesticidally effective amount of at least one compound of the formula I,a stereoisomer thereof and/or at least one agriculturally acceptablesalt thereof.
 32. The method as claimed in claim 30, for protectingplant propagation material and/or the plants which grow therefrom fromattack or infestation by invertebrate pests, which method comprisestreating the plant propagation material with a pesticidally effectiveamount of at least one compound of the formula I, a stereoisomer thereofand/or at least one agriculturally acceptable salt thereof.
 33. Plantpropagation material treated with at least one compound of the formula Ias defined in claim 1, a stereoisomer thereof and/or at least oneagriculturally acceptable salt thereof.